(3,3-dimethyl-2,4-dioxolanyl)methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

• 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: (3,3-dimethyl-2,4-dioxolanyl)methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-6-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-2-phenyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• 化学式: C₃₃H₃₈O₈
• 分子量: 562.66
• InChiKey: UYDWMMFUFBTJJW-XXHBPBJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  α-D(+)-五乙酰葡萄糖 在 甲醇 、 Oxone 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 、 camphor-10-sulfonic acid 、 sodium 、 四氯化锡 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 (3,3-dimethyl-2,4-dioxolanyl)methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Chemistry of 4,6-O-Benzylidene-d-glycopyranosyl Triflates:  Contrasting Behavior between the Gluco and Manno Series

  摘要：

  Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 degrees C in the presence of 2,6-di-tert-butyl-4-methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides cl-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the beta-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.

  DOI：

  10.1021/jo990243d

文献信息

• Chemistry of 4,6-<i>O</i>-Benzylidene-<scp>d</scp>-glycopyranosyl Triflates:  Contrasting Behavior between the Gluco and Manno Series
  作者：David Crich、Weiling Cai

  DOI：10.1021/jo990243d

  日期：1999.6.1

  Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 degrees C in the presence of 2,6-di-tert-butyl-4-methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides cl-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the beta-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.