propyl 2-O-acetyl-3,4,6-tri-O-benzoyl-β-D-mannopyranoside | 215721-39-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: propyl 2-O-acetyl-3,4,6-tri-O-benzoyl-β-D-mannopyranoside
• CAS: 215721-39-4
• 化学式: C₃₂H₃₂O₁₀
• 分子量: 576.6
• InChiKey: YJCQWFQKCBAXRQ-KJSPXZFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  allyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 25.0h， 生成 propyl 2-O-acetyl-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