benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside | 86420-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
• 英文别名: (2R,4aR,6R,7R,8S,8aS)-2-phenyl-6,7-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 86420-81-7
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: IJTAXRQQXZVWQA-BLQNYSDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 盐酸 、 甲醇 、 silver trifluoromethanesulfonate 、 sodium hydride 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.42h， 生成 benzyl 2,6-di-O-benzyl-3-O-methyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-O-β-d-galactopyranosyl-3-O-methyl-d-glucose

  摘要：

  DOI：

  10.1016/0008-6215(85)85168-5
• 作为产物：
  描述：

  苄基 alpha-D-吡喃葡萄糖苷 在 甲醇 、 sodium hydroxide 、 四丁基硫酸氢铵 、 对甲苯磺酸 作用下， 反应 5.0h， 生成 benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 4-O-β-d-galactopyranosyl-3-O-methyl-d-glucose

  摘要：

  DOI：

  10.1016/0008-6215(85)85168-5

文献信息

• A reinvestigation of glycosidation reactions using 1-thioglycosides as glycosyl donors and thiophilic cations as promoters
  作者：Per J. Garegg、Christina Henrichson、Thomas Norberg

  DOI：10.1016/s0008-6215(00)90965-0

  日期：1983.5
• Grindley, T. Bruce; Thangarasa, Rasiah, Canadian Journal of Chemistry, 1990, vol. 68, # 7, p. 1007 - 1019
  作者：Grindley, T. Bruce、Thangarasa, Rasiah

  DOI：——

  日期：——
• A novel promoter for the efficient construction of 1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl donors
  作者：Peter Fügedi、Per J. Garegg

  DOI：10.1016/s0008-6215(00)90385-9

  日期：1986.6
• The First Total Syntheses of Enantiomerically Pure Naturally Occuring Ellagitannins Gemin D and its Regioisomer Hippomanin A
  作者：Karamali Khanbabaee、Kerstin Lötzerich、Markus Borges、Mathias Großer

  DOI：10.1002/(sici)1521-3897(199902)341:2<159::aid-prac159>3.0.co;2-6

  日期：1999.2

  The total syntheses of naturally occuring ellagitannins gemin D (1) and its regioisomer hippomanin A (2) are reported. In addition, the phase-transfer catalyzed benzylation reaction of the 2,3-glucopyranoside diols 3-7 is described. Our studies have illustrated the influence of the structure of 2,3-glucopyranoside diols on the regioselectivity of the phase-transfer catalyzed benzylation at their free 2,3-OH groups. We could show, that both phase-transfer catalyzed benzylations of 2,3-glucopyranoside diols using tetrabutylammonium hydrogensulfate (Bu4NHSO4) or using tetrabutylammonium iodide (Bu4NI) disfavour the formation of the corresponding 3-O-monobenzylated products and preferentially give the 2-O-monobenzylated products. However, the ratio of the generated 2- versus 3-O-mono- and 2,3-dibenzylated products from these reactions also strongly depends upon the nature of the starting materials. The glucopyranosides 3 and 4 are the first examples, which allow the completely regioselective monobenzyIation at the 2-OH positions by a phase-transfer catalyzed reaction.
• Double diastereoselection explains limitations in synthesizing mannose-containing β-(1,3)-glucans
  作者：Balla Sylla、Karine Descroix、Christophe Pain、Cédric Gervaise、Frank Jamois、Jean-Claude Yvin、Laurent Legentil、Caroline Nugier-Chauvin、Richard Daniellou、Vincent Ferrières

  DOI：10.1016/j.carres.2010.04.018

  日期：2010.7

  It is known that 3-O-glycosylation of glucosidic acceptors bearing acyl groups in the 4 and 6 positions instead of a 4,6-O-benzylidene ring mainly affords a-glycosides. Described here is an unexpected stereochemical outcome for elongation at glucose O-3 of a beta-D-Glcp-(1 -> 3)-alpha-D-Manp disaccharide using peracetylated ethyl thioglucoside as a donor. This unexpected reaction was correlated with match-mismatch effects, as shown by efficient coupling of the same acceptor by a donor of L-configuration. (C) 2010 Elsevier Ltd. All rights reserved.