trans-2'-butenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside | 136764-25-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: trans-2'-butenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: trans-crotyl-3,4,6-tri-O-benzyl-β-D-glucopyranose；(2R,3R,4R,5R,6R)-2-[(E)-but-2-enoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 136764-25-5
• 化学式: C₃₁H₃₆O₆
• 分子量: 504.623
• InChiKey: JRXCKIXQXCVLOE-MAGWVKRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：

  trans-2'-butenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 3A mol. siev 、 间氯过氧苯甲酸 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以80%的产率得到(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(3-methyl-oxiranylmethoxy)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  碳水化合物作为手性助剂：烯烃的不对称环氧化反应

  摘要：

  在优化条件下，1-环氧化ø -反式-2-丁烯基-3,4,6-三ö苄基β-d-D-吡喃葡萄糖，得到9:1非对映体的1:1混合物。观察到的非对映选择性高度依赖于所用试剂的性质以及助剂C --2处的保护基团。

  DOI：

  10.1016/s0957-4166(00)80083-x
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucopyranose 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 trans-2'-butenyl-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

文献信息

• Carbohydrates as chiral auxiliaries: The asymmetric epoxidation reaction of olefins
  作者：André B. Charette、Bernard Côté

  DOI：10.1016/s0957-4166(00)80083-x

  日期：1993.11

  ucopyranose gave a 9:1 mixture of diastereomers. The diastereoselectivities observed were shown to be highly dependent on the nature of the reagent used and of the protecting group at C-2 of the auxiliary.

  在优化条件下，1-环氧化ø -反式-2-丁烯基-3,4,6-三ö苄基β-d-D-吡喃葡萄糖，得到9:1非对映体的1:1混合物。观察到的非对映选择性高度依赖于所用试剂的性质以及助剂C --2处的保护基团。
• Carbohydrates as chiral auxiliaries: synthesis of 2-hydroxy-β-D-glucopyranosides
  作者：André B. Charette、Jean-François Marcoux、Bernard Côté

  DOI：10.1016/0040-4039(91)80479-p

  日期：1991.12

  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).
• An efficient stereoselective synthesis of enantiomerically pure aziridine derivatives of allyl β-d-glucopyranosides asymmetrically induced by a glucide moiety
  作者：Cinzia Chiappe、Paolo Crotti、Elena Menichetti、Mauro Pineschi

  DOI：10.1016/s0957-4166(98)00427-3

  日期：1998.11

  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.