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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。

Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

机构信息

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

出版信息

J Org Chem. 2010 Dec 17;75(24):8383-91. doi: 10.1021/jo101453y. Epub 2010 Nov 11.

DOI:10.1021/jo101453y
PMID:21070063
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3064765/
Abstract

α-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.

摘要

α-C-吡喃葡萄糖苷和α-D-吡喃甘露糖苷可以通过 4,6-O-苄叉保护的 3-O-位带有酯基的葡萄糖基和甘露糖基硫糖苷与 C-亲核试剂在二苯砜、2,4,6-三特丁基嘧啶和三氟甲磺酸酐的活化作用下发生偶联反应，以 65-85%的收率得到。

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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。
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2
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本文引用的文献

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Mechanism of a chemical glycosylation reaction.化学糖基化反应的机制。
Acc Chem Res. 2010 Aug 17;43(8):1144-53. doi: 10.1021/ar100035r.
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Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.通过 4,5-O-碳酸酯保护基对 alpha-酮去氧-D-甘油-D-半乳糖-壬酮糖苷进行立体选择性合成。
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Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit.亲核性增加导致立体化学控制的侵蚀：扩散限制下的 O-糖基化。
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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.
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Beta-directing effect of electron-withdrawing groups at O-3, O-4, and O-6 positions and alpha-directing effect by remote participation of 3-O-acyl and 6-O-acetyl groups of donors in mannopyranosylations.β-位吸电子基团（O-3、O-4 和 O-6 位）和α-位供体 3-O-酰基和 6-O-乙酰基的远程参与的给电子基团的 directing effect 在吡喃甘露糖苷化反应中的作用。
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Correlations between nucleophilicities and selectivities in the substitutions of tetrahydropyran acetals.四氢吡喃缩醛取代反应中亲核性和选择性的相关性。
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Computational studies of the role of glycopyranosyl oxacarbenium ions in glycobiology and glycochemistry.吡喃糖基氧碳鎓离子在糖生物学和糖化学中作用的计算研究
Adv Carbohydr Chem Biochem. 2009;62:83-159. doi: 10.1016/S0065-2318(09)00004-3.
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J Org Chem. 2009 Jan 16;74(2):545-53. doi: 10.1021/jo8017846.
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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。
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