benzyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside | 1093186-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl β-D-galactopyranosyl-(1->6)-β-D-glucopyranoside
• 英文别名: benzyl β-D-Galp-(1->6)-β-D-Glcp
• CAS: 1093186-54-9
• 化学式: C₁₉H₂₈O₁₁
• 分子量: 432.425
• InChiKey: LLEMMFPELBNINR-WLYRFEJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.17
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  178.53
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  α-galactosyl fluoride 、 苄基 alpha-D-吡喃葡萄糖苷 在 E338 mutant TtβGly glycosidase from Thermus thermophilus 作用下， 反应 12.0h， 以55%的产率得到benzyl β-D-galactopyranosyl-(1->3)-β-D-glucopyranoside
  参考文献：
  名称：

  Engineering of glucoside acceptors for the regioselective synthesis of β-(1→3)-disaccharides with glycosynthases

  摘要：

  Glycosynthase mutants obtained from Thermotoga maritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1 -> 3)-beta-D-Glcp and aryl beta-D-Glcp-(1 -> 3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-D-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1 -> 3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.07.018

文献信息

• Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions
  作者：Kalyan Dey、Narayanaswamy Jayaraman

  DOI：10.1039/d1cc07056h

  日期：——

  A site-specific deprotonation followed by alkylations and acylations of sugar hemiacetals to the corresponding alkyl glycosides and acylated sugars in aqueous solutions is disclosed herein. Pyridoneimine as a new base is developed to mediate the deprotonation of readily available sugar hemiacetals and further reactions with alkylation and acylation agents.

  本文公开了在水溶液中进行位点特异性去质子化，随后将糖半缩醛烷基化和酰化为相应的烷基糖苷和酰化糖。吡啶酮亚胺作为一种新的碱被开发用于介导容易获得的糖半缩醛的去质子化以及与烷基化和酰化剂的进一步反应。