2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6S)-6-[[(4aR,6S,7R,8S,8aR)-2,2-dimethyl-8-phenylmethoxy-6-prop-2-enoxycarbonyloxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]oxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₅₄H₅₂O₁₇
• 分子量: 972.997
• InChiKey: BGMRGQIFWHFTCD-CFMNDZEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  71
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  3-O-benzyl-4,6-O-isopropylidene-D-glucopyranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->2)-1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose
  参考文献：
  名称：

  Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

  摘要：

  A highly regio- and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-alpha,beta-D-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-beta-acetates or -carbonates in excellent yields. The 2-OH, 1-beta-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl trichloroacetimidates by reaction with trichloroacetonitrile via base promoted acetyl migration, while the 2-OH, 1-beta-carbonates were good glycosyl acceptors for the synthesis of (1 -> 2)-linked oligosaccharides. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.01.010

文献信息

• Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols
  作者：Jianjun Zhang、Xiaomei Liang、Daoquan Wang、Fanzuo Kong

  DOI：10.1016/j.carres.2007.01.010

  日期：2007.5

  A highly regio- and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-alpha,beta-D-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-beta-acetates or -carbonates in excellent yields. The 2-OH, 1-beta-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl trichloroacetimidates by reaction with trichloroacetonitrile via base promoted acetyl migration, while the 2-OH, 1-beta-carbonates were good glycosyl acceptors for the synthesis of (1 -> 2)-linked oligosaccharides. (c) 2007 Elsevier Ltd. All rights reserved.