2'-methylpropenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside | 220368-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-methylpropenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-2-(2-methylprop-2-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 220368-50-3
• 化学式: C₃₁H₃₆O₆
• 分子量: 504.623
• InChiKey: CWSCMRVCZXWDAF-JQWMYKLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  2'-methylpropenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium azide 、 一氯化碘 作用下， 以 乙腈 为溶剂， 以90%的产率得到3'-iodo-2'-methyl-2'-azidopropyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  An efficient stereoselective synthesis of enantiomerically pure aziridine derivatives of allyl β-d-glucopyranosides asymmetrically induced by a glucide moiety

  摘要：

  The enantiomerically pure title aziridines were obtained by regioselective azidolysis of the 2',3'-epoxy derivatives of allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranosides, followed by cyclization of the corresponding azido alcohols by means of the PPh3 protocol. Enantiomerically pure starting epoxides were prepared by epoxidation of the corresponding allyl 3,4,6-tri-O-benzyl-beta-D-glucopyranosides asymmetrically induced by a glucide moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00427-3
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-2-(2-methylprop-2-enoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 2'-methylpropenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrates as chiral auxiliaries: synthesis of 2-hydroxy-β-D-glucopyranosides

  摘要：

  A new 2-step, 1-pot procedure for the stereoselective glycosylation of allylic alcohols with 1,2-di-O-benzoyl-beta-D-glucopyranosides to produce 2-hydroxy-beta-D-glucopyranosides has been developed. The required precursor for the glycosylation was readily obtained from tri-O-benzyl-D-glucal in 2 steps (91% overall).

  DOI：

  10.1016/0040-4039(91)80479-p