• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

高立体选择性合成α-D-甘露吡喃糖基磷酸糖。

Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.

机构信息

Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette, France.

出版信息

J Org Chem. 2009 Dec 18;74(24):9576-9. doi: 10.1021/jo902254w.

DOI:10.1021/jo902254w
PMID:19924835
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2852025/
Abstract

Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.

摘要

α-甘露糖基磷酸糖酯可从 3-O 位带有酯基官能团的 4,6-O-亚苄基保护的甘露糖基硫糖苷经与磷酸糖盐的偶联反应以 1-苯磺酰基哌啶、2,4,6-三特丁基嘧啶和三氟甲磺酸酐活化后以 61-90%的收率获得。由于存在非致死性酯基，仅观察到α-异构体的形成。

相似文献

1
Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.高立体选择性合成α-D-甘露吡喃糖基磷酸糖。
J Org Chem. 2009 Dec 18;74(24):9576-9. doi: 10.1021/jo902254w.
2
1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.1-苯亚磺酰基哌啶/三氟甲磺酸酐：一种用于将硫代糖苷低温转化为糖基三氟甲磺酸酯以及形成多种糖苷键的稳定试剂的有效组合。
J Am Chem Soc. 2001 Sep 19;123(37):9015-20. doi: 10.1021/ja0111481.
3
Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.O3 保护基对 4,6-O-苄叉基保护供体制备 C-吡喃甘露糖苷的立体选择性的影响。
J Org Chem. 2010 Dec 17;75(24):8383-91. doi: 10.1021/jo101453y. Epub 2010 Nov 11.
4
Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.合成鼠伤寒沙门氏菌E(1)型核心三糖，作为1-(苯亚磺酰基)哌啶/三氟甲磺酸酐组合用于从硫代糖苷形成糖苷键的通用性研究的探针。
J Org Chem. 2002 Jul 12;67(14):4640-6. doi: 10.1021/jo0108818.
5
Synthesis and glycosylation of a series of 6-mono-, di-, and trifluoro S-phenyl 2,3,4-tri-O-benzyl-thiorhamnopyranosides. Effect of the fluorine substituents on glycosylation stereoselectivity.一系列6-单氟、二氟和三氟的S-苯基2,3,4-三-O-苄基硫代鼠李糖苷的合成与糖基化。氟取代基对糖基化立体选择性的影响。
J Am Chem Soc. 2007 Sep 26;129(38):11756-65. doi: 10.1021/ja0730258. Epub 2007 Aug 29.
6
On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation.关于C2 - O2和C3 - O3键在4,6 - O - 亚苄基导向的β - 甘露吡喃糖基化和α - 葡糖吡喃糖基化中的影响
J Org Chem. 2006 Oct 27;71(22):8473-80. doi: 10.1021/jo061417b.
7
Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/trimethylsilyl triflate.4,6-O-亚苄基、4,6-O-苯基硼酸酯和4,6-O-聚苯乙烯基硼酸酯保护基对由1-苯亚磺酰基哌啶/三氟甲磺酸酐以及N-碘代琥珀酰亚胺/三甲基甲硅烷基三氟甲磺酸酯介导的基于硫代糖苷的糖基化反应的立体化学结果的影响。
J Org Chem. 2003 Oct 17;68(21):8142-8. doi: 10.1021/jo0349882.
8
Determination of the Influence of Side-Chain Conformation on Glycosylation Selectivity using Conformationally Restricted Donors.使用构象受限供体确定侧链构象对糖基化选择性的影响
Chemistry. 2016 Mar 18;22(13):4535-42. doi: 10.1002/chem.201505019. Epub 2016 Feb 16.
9
Influence of protecting groups on the reactivity and selectivity of glycosylation: chemistry of the 4,6-o-benzylidene protected mannopyranosyl donors and related species.保护基对糖基化反应活性和选择性的影响：4,6-O-亚苄基保护的甘露吡喃糖基供体及相关物种的化学性质
Top Curr Chem. 2011;301:141-88. doi: 10.1007/128_2010_102.
10
Is donor-acceptor hydrogen bonding necessary for 4,6-O-benzylidene-directed beta-mannopyranosylation? Stereoselective synthesis of beta-C-mannopyranosides and alpha-C-glucopyranosides.对于4,6-O-亚苄基导向的β-甘露吡喃糖基化反应，供体-受体氢键是必要的吗？β-C-甘露吡喃糖苷和α-C-葡萄糖吡喃糖苷的立体选择性合成。
Org Lett. 2008 Nov 6;10(21):4731-4. doi: 10.1021/ol8017038. Epub 2008 Oct 1.

引用本文的文献

1
Recent advances in chemical synthesis of phosphodiester linkages found in fungal mannans.真菌甘露聚糖中磷酸二酯键化学合成的最新进展。
Carbohydr Res. 2025 Jan;547:109325. doi: 10.1016/j.carres.2024.109325. Epub 2024 Nov 22.
2
Synthetic Neoglycoconjugates of Hepta- and Nonamannoside Ligands for Eliciting Oligomannose-Specific HIV-1-Neutralizing Antibodies.七糖和九糖配体的合成糖缀合物，用于诱导寡甘露糖特异性 HIV-1 中和抗体。
Chembiochem. 2022 Apr 5;23(7):e202200061. doi: 10.1002/cbic.202200061. Epub 2022 Feb 11.
3
Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides.立体选择性金（I）催化合成复杂的α-糖苷基磷酸酯。
Nat Commun. 2022 Jan 20;13(1):421. doi: 10.1038/s41467-022-28025-0.
4
Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(CF)-catalyzed glycosylation of sterically-hindered precursors.通过空间位阻前体的B(CF)催化糖基化反应快速组装免疫佐剂酸枣仁皂苷A的双分支五糖结构域
Chem Commun (Camb). 2017 May 30;53(43):5838-5841. doi: 10.1039/c7cc01783a.
5
Bioresponsive deciduous-charge amphiphiles for liposomal delivery of DNA and siRNA.生物响应性季铵盐两亲物用于 DNA 和 siRNA 的脂质体递送
Pharm Res. 2013 May;30(5):1362-79. doi: 10.1007/s11095-013-0976-9. Epub 2013 Feb 1.
6
Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.O3 保护基对 4,6-O-苄叉基保护供体制备 C-吡喃甘露糖苷的立体选择性的影响。
J Org Chem. 2010 Dec 17;75(24):8383-91. doi: 10.1021/jo101453y. Epub 2010 Nov 11.

本文引用的文献

1
New principles for glycoside-bond formation.糖苷键形成的新原理。
Angew Chem Int Ed Engl. 2009;48(11):1900-34. doi: 10.1002/anie.200802036.
2
Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.非邻位酯的邻基参与在糖基化反应中起作用吗？用于检测桥连中间体的有效探针。
J Org Chem. 2008 Nov 21;73(22):8942-53. doi: 10.1021/jo801630m. Epub 2008 Oct 22.
3
Block synthesis of tetra- and hexasaccharides (beta-D-glycero-D-manno-Hep p-(1-->4)-[alpha-l-Rha p-(1-->3)-beta-D-glycero-D-manno-Hep p-(1-->4)]n-alpha-L-Rha p-OMe (n = 1 and 2)) corresponding to multiple repeat units of the glycan from the surface-layer glycoprotein from Bacillus thermoaerophilus.合成嗜热栖热芽孢杆菌表层糖蛋白聚糖多个重复单元对应的四糖和六糖（β-D-甘油-D-甘露庚糖p-(1→4)-[α-L-鼠李糖p-(1→3)-β-D-甘油-D-甘露庚糖p-(1→4)]n-α-L-鼠李糖p-OMe，n = 1和2）。
J Org Chem. 2008 Sep 19;73(18):7003-10. doi: 10.1021/jo801414c. Epub 2008 Aug 27.
4
Structural analysis of the capsular polysaccharide from Campylobacter jejuni RM1221.空肠弯曲菌RM1221荚膜多糖的结构分析。
Chembiochem. 2007 Apr 16;8(6):625-31. doi: 10.1002/cbic.200600508.
5
Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis.含有糖基磷酸单元的天然磷酸聚糖：结构多样性与化学合成
Carbohydr Res. 2007 Feb 26;342(3-4):297-344. doi: 10.1016/j.carres.2006.10.006. Epub 2006 Oct 12.
6
Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.D-和L-甘油-β-D-甘露庚吡喃糖苷及其6-脱氧类似物的立体控制合成。α-L-鼠李吡喃糖基-(1→3)-D-甘油-β-D-甘露庚吡喃糖基-(1→3)-6-脱氧甘油-β-D-甘露庚吡喃糖基-(1→4)-α-L-鼠李吡喃糖苷的合成，嗜水气单胞菌脂多糖的四糖亚基。
J Am Chem Soc. 2006 Jun 21;128(24):8078-86. doi: 10.1021/ja061594u.
7
Synthesis and stereoselective glycosylation of D- and L-glycero-beta-D-manno-heptopyranoses.D-和L-甘油-β-D-甘露庚吡喃糖的合成及立体选择性糖基化反应
Org Lett. 2005 Mar 31;7(7):1395-8. doi: 10.1021/ol050224s.
8
Synthesis of proteophosphoglycans of Leishmania major and Leishmania mexicana.硕大利什曼原虫和墨西哥利什曼原虫蛋白磷酸聚糖的合成
J Org Chem. 2005 Mar 4;70(5):1691-7. doi: 10.1021/jo048443z.
9
Direct chemical synthesis of the beta-mannans: linear and block syntheses of the alternating beta-(1-->3)-beta-(1-->4)-mannan common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexa.β-甘露聚糖的直接化学合成：对粘红酵母、粘质红酵母和双曲钩端螺旋体中常见的交替β-(1→3)-β-(1→4)-甘露聚糖进行线性和嵌段合成。
J Am Chem Soc. 2004 Nov 24;126(46):15081-6. doi: 10.1021/ja0471931.
10
Benzylidene acetal fragmentation route to 6-deoxy sugars: direct reductive cleavage in the presence of ether protecting groups, permitting the efficient, highly stereocontrolled synthesis of beta-D-rhamnosides from D-mannosyl glycosyl donors. Total synthesis of alpha-D-Gal-(1-->3)-alpha-D-Rha-(1-->3)- beta-D-Rha-(1-->4)-beta-D-Glu-OMe, the repeating unit of the antigenic lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652.通向6-脱氧糖的亚苄基缩醛断裂途径：在醚保护基存在下的直接还原裂解，可从D-甘露糖基糖基供体高效、高度立体选择性地合成β-D-鼠李糖苷。来自赫氏埃希菌ATCC 33650和33652的抗原性脂多糖重复单元α-D-半乳糖-（1→3）-α-D-鼠李糖-（1→3）-β-D-鼠李糖-（1→4）-β-D-葡萄糖-OMe的全合成。
J Am Chem Soc. 2004 Jul 7;126(26):8232-6. doi: 10.1021/ja048070j.