1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose | 934491-94-8

• 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: 1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose
• 英文别名: [(4aR,6S,7R,8R,8aR)-7-hydroxy-2,2-dimethyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] prop-2-enyl carbonate
• CAS: 934491-94-8
• 化学式: C₂₀H₂₆O₈
• 分子量: 394.422
• InChiKey: UXOOTRGKRYNIBF-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-allyloxycarbonyl-3-O-benzyl-4,6-O-isopropylidene-β-D-glucopyranose 、 2,3,4,6-tetra-O-benzoyl-D-mannopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(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
• 作为产物：
  描述：

  氯甲酸烯丙酯 、 3-O-benzyl-4,6-O-isopropylidene-D-glucopyranose 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以86%的产率得到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

• Practical preparation of 2-azido-2-deoxy-β-d-mannopyranosyl carbonates and their application in the synthesis of oligosaccharides
  作者：Jianjun Zhang、Shiqiang Yan、Xiaomei Liang、Jingping Wu、Daoquan Wang、Fanzuo Kong

  DOI：10.1016/j.carres.2007.09.001

  日期：2007.12

  1-O-Allyloxycarbonyl (or ethyloxycarbonyl)-2-azido-2-deoxy-3-O-benzyl (or allyl, or benzoyl)-4,6-O-isopropylidene-beta-d-mannopyranose derivatives were prepared from the corresponding 2-hydroxy-beta-d-glucopyranosyl carbonates in high yields via triflation of the 2-hydroxyl group and subsequent SN2 displacement with azide ion. An N-acetyl-mannosamine-containing trisaccharide, a fragment of the putative

  从相应的化合物制备1-O-烯丙氧羰基（或乙氧羰基）-2-叠氮基-2-脱氧-3-O-苄基（或烯丙基或苯甲酰基）-4，6-O-异亚丙基-β-d-甘露吡喃糖衍生物。通过2-羟基的三氟甲磺酸化和随后的叠氮化物离子取代SN2，可以高产率地生成2-羟基-β-d-吡喃葡萄糖基碳酸酯。使用这些衍生物有效地合成了含有N-乙酰基-甘露糖胺的三糖，其是鲍曼不动杆菌推定的O10抗原的片段。
• 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.