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通过螺环丙烷的氢解裂解合成2-乙酰新壳二糖衍生物

Synthesis of 2-acetylnoviosamine derivatives by hydrogenolytic cleavage of a spirocyclopropane.

作者信息

Salim Maruan D, Ferrara Isabella, Blacque Olivier, Gademann Karl

机构信息

Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zürich, Switzerland.

出版信息

Org Biomol Chem. 2025 May 21;23(20):4873-4878. doi: 10.1039/d5ob00469a.

DOI:10.1039/d5ob00469a
PMID:40289689
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12035602/
Abstract

The preparation of a 2-acetamido derivative of the rare 5,5--dimethyl-deoxy carbohydrate noviose is reported in this study. The synthesis starts from readily available -acetyl-D-mannosamine and tackles the introduction of the -dimethyl structural feature a cyclopropanation and hydrogenolytic cleavage strategy, which can enable the synthesis of 2-amino noviose derivatives of both L- and D-noviose.

摘要

本研究报道了稀有5,5-二甲基脱氧碳水化合物新霉糖的2-乙酰氨基衍生物的制备。合成从容易获得的N-乙酰-D-甘露糖胺开始，并采用环丙烷化和氢解裂解策略引入5,5-二甲基结构特征，该策略能够合成L-和D-新霉糖的2-氨基新霉糖衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/45ce02633c3a/d5ob00469a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/62a26504cf26/d5ob00469a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/263c6818e311/d5ob00469a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/45ce02633c3a/d5ob00469a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/62a26504cf26/d5ob00469a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/263c6818e311/d5ob00469a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ae3d/12035602/45ce02633c3a/d5ob00469a-f3.jpg

相似文献

1
Synthesis of 2-acetylnoviosamine derivatives by hydrogenolytic cleavage of a spirocyclopropane.通过螺环丙烷的氢解裂解合成2-乙酰新壳二糖衍生物
Org Biomol Chem. 2025 May 21;23(20):4873-4878. doi: 10.1039/d5ob00469a.
2
A convenient synthesis of N-acetyllactosamine derivatives from lactal.一种从乳醛方便地合成N-乙酰乳糖胺衍生物的方法。
Carbohydr Res. 1993 Sep 2;247:159-64. doi: 10.1016/0008-6215(93)84249-6.
3
Some further studies on the synthesis of glycopeptide derivatives: 2-acetamido-2-deoxy-beta-D-glucopyranosylamine derivatives.关于糖肽衍生物合成的进一步研究：2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖胺衍生物
Biochem J. 1966 Oct;101(1):184-90. doi: 10.1042/bj1010184.
4
Synthesis of C-3 nitrogen-containing derivatives of N-acetyl-alpha,beta-D-mannosamine as substrates for N-acetylneuraminic acid aldolase.N-乙酰-α,β-D-甘露糖胺的C-3含氮衍生物作为N-乙酰神经氨酸醛缩酶底物的合成。
Carbohydr Res. 2001 May 18;332(2):133-9. doi: 10.1016/s0008-6215(01)00091-x.
5
Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-D-mannopyranose and the 3-position of 2-acetamido-2-deoxy-D-mannose: potential membrane modifiers in neoplastic control.2-氨基-2-脱氧-D-甘露吡喃糖氨基功能和2-乙酰氨基-2-脱氧-D-甘露糖3位选择性修饰中的多功能中间体：肿瘤控制中的潜在膜修饰剂
Carbohydr Res. 1995 Oct 16;276(1):99-115. doi: 10.1016/0008-6215(95)00154-l.
6
Synthetic mucin fragments. Benzyl O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[(2-acetamido-2-deoxy-beta-D-glucopyran osy l)- (1----6)]-2-acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[beta-D-galactopyranosyl-(1----6)]-2-ac eta mido- 2-deoxy-alpha-D-galactopyranoside.合成粘蛋白片段。苄基 O-(2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基)-(1→3)-O-β-D-吡喃半乳糖基-(1→3)-O-[(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→6)]-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷和苄基 O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→3)-O-β-D-吡喃半乳糖基-(1→3)-O-[β-D-吡喃半乳糖基-(1→6)]-2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖苷。
Carbohydr Res. 1988 Dec 1;183(2):163-73. doi: 10.1016/0008-6215(88)84071-0.
7
Synthesis of a fully protected derivative of O-(N-acetyl-alpha-D-neuraminyl)-(2----3)-O-beta-D-galactopyranosyl-(1- ---3)-O- [(N-acetyl-alpha-D-neuraminyl)-(2----6)]-O-(2-acetamido-2-deoxy-alpha- D-galactopyranosyl)-(1----3)-L-serine.O-（N-乙酰基-α-D-神经氨酰基）-（2→3）-O-β-D-吡喃半乳糖基-（1→3）-O- [（N-乙酰基-α-D-神经氨酰基）-（2→6）]-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1→3）-L-丝氨酸的全保护衍生物的合成
Carbohydr Res. 1989 Feb 15;186(1):107-18. doi: 10.1016/0008-6215(89)84009-1.
8
Synthesis of benzyl 2-acetamido-2-deoxy-3-O-beta-D-fucopyranosyl-alpha-D-galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta- D-glucopyranosyl)-2-deoxy-3-O-beta-D-fucopyranosyl-alpha-D- galactopyranoside.2-乙酰氨基-2-脱氧-3-O-β-D-岩藻糖基-α-D-吡喃半乳糖苷苄酯和2-乙酰氨基-6-O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-2-脱氧-3-O-β-D-岩藻糖基-α-D-吡喃半乳糖苷苄酯的合成
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Concise and efficient synthesis of 2-acetamido-2-deoxy-beta-D-hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-beta-D-glucose.从2-乙酰氨基-2-脱氧-β-D-葡萄糖简洁高效地合成多种氨基糖的2-乙酰氨基-2-脱氧-β-D-己吡喃糖苷。
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Synthesis of a fucosylated and a non-fucosylated core structure of xylose-containing carbohydrate chains from N-glycoproteins.从N-糖蛋白合成含木糖碳水化合物链的岩藻糖基化和非岩藻糖基化核心结构。
Carbohydr Res. 1994 Nov 1;264(1):45-62. doi: 10.1016/0008-6215(94)00187-1.

本文引用的文献

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Formal Single Atom Editing of the Glycosylated Natural Product Fidaxomicin Improves Acid Stability and Retains Antibiotic Activity.糖基化天然产物非达霉素的形式单原子编辑提高了酸稳定性并保留了抗生素活性。
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