Trifluoro-methanesulfonic acid (3aS,3bS,6S,6aS,7aS)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester | 202063-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: Trifluoro-methanesulfonic acid (3aS,3bS,6S,6aS,7aS)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester
• CAS: 202063-28-3
• 化学式: C₁₀H₁₁F₃O₈S
• 分子量: 348.254
• InChiKey: KFJYNWHWYGYVJE-PEOQWYCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.02
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aS,3bS,6S,6aS,7aS)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (3aS,3bS,6R,6aR,7aS)-6-Azido-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one
  参考文献：
  名称：

  Mannuronolactone acetonide: easy access to C-3 OH and C-5 OH of mannose

  摘要：

  The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-beta-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-beta-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-beta-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00604-6
• 作为产物：
  描述：

  D-mannofuranurono-6,3-lactone 在 吡啶 、 camphor-10-sulfonic acid 、 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 21.08h， 生成 Trifluoro-methanesulfonic acid (3aS,3bS,6S,6aS,7aS)-2,2-dimethyl-5-oxo-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Mannuronolactone acetonide: easy access to C-3 OH and C-5 OH of mannose

  摘要：

  The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-beta-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-beta-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-beta-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00604-6

文献信息

• Caesium Trifluoroacetate Displacement of Triflates in the Inversion of Alcohols
  作者：Andrew Bell、Lea Pickering、Malcolm Finn、Carmen de la Fuente、Thomas Krülle、Benjamin Davis、G. Fleet

  DOI：10.1055/s-1997-1541

  日期：1997.9

  Caesium trifluoroacetate has advantages over both sodium trifluoroacetate and caesium acetate for the efficient inversion of configuration of alcohols by displacement of triflates.

  与三氟乙酸钠和醋酸铯相比，三氟乙酸铯在通过置换三氟酸盐来有效反转醇的构型方面具有优势。