propyl 3,4,6-tri-O-benzoyl-β-D-mannopyranoside | 215721-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 3,4,6-tri-O-benzoyl-β-D-mannopyranoside
• CAS: 215721-41-8
• 化学式: C₃₀H₃₀O₉
• 分子量: 534.563
• InChiKey: LZEUZIUHEGMBEB-QKSWYADASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  117.59
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  propyl 3,4,6-tri-O-benzoyl-β-D-mannopyranoside 在 吡啶 、 盐酸 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.33h， 生成
  参考文献：
  名称：

  Synthesis of a dithio analogue of n-propyl kojibioside as a potential glucosidase I inhibitor

  摘要：

  Procedures for the preparation of 3,4,6-protected 2-thio-alpha-D-glucopyranoside derivatives by thiolate nucleophilic displacement of the 2-O-triflate of alpha-D-mannopyranoside derivatives were investigated. A synthesis of n-propyl 3,4,6-tri-O-benzyl-2-thio-beta-D-glucopyran was developed. Glycosylation of this derivative with 2,3,4,6-tetra-O-acetyl-5-thio-alpha-D -glucopyranosyl trichloro-acetimidate gave an alpha/beta mixture of protected n-propyl beta-dithiokojibioside and beta-dithiosophoroside. Deprotection of the mixture by standard methods and separation by chromatography gave n-propyl beta-dithiokojibioside (1) which is a potential enzyme inhibitor of glucosidase I. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00165-7
• 作为产物：
  描述：

  propyl 2-O-acetyl-3,4,6-tri-O-benzoyl-β-D-mannopyranoside 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 以89%的产率得到propyl 3,4,6-tri-O-benzoyl-β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a dithio analogue of n-propyl kojibioside as a potential glucosidase I inhibitor

  摘要：

  Procedures for the preparation of 3,4,6-protected 2-thio-alpha-D-glucopyranoside derivatives by thiolate nucleophilic displacement of the 2-O-triflate of alpha-D-mannopyranoside derivatives were investigated. A synthesis of n-propyl 3,4,6-tri-O-benzyl-2-thio-beta-D-glucopyran was developed. Glycosylation of this derivative with 2,3,4,6-tetra-O-acetyl-5-thio-alpha-D -glucopyranosyl trichloro-acetimidate gave an alpha/beta mixture of protected n-propyl beta-dithiokojibioside and beta-dithiosophoroside. Deprotection of the mixture by standard methods and separation by chromatography gave n-propyl beta-dithiokojibioside (1) which is a potential enzyme inhibitor of glucosidase I. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00165-7