Methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-yl ester | 616238-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-yl ester
• CAS: 616238-07-4
• 化学式: C₃₆H₄₀O₈S₂
• 分子量: 664.841
• InChiKey: DYPQUJRITSSXLN-GJXDWMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  46.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 Methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-yl ester 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran
  参考文献：
  名称：

  A General Method for the Synthesis of Sugar 2-C-Sulfonic Acids by 1 → 2 Arylthio Group Migration in Acid-Sensitive Thioglycosides.¹ Direct Transformation of Thiotrityl Ethers into C-Sulfonic Acids

  摘要：

  Fully protected triphenylmethyl 2-O-mesyl-1-thio-beta-D-gluco- (14) and -alpha-D-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 --> 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-alpha-D-manno- (15) and -beta-D-glucopyranoside (29), respectively, using NaOCH3 as nucleophile. The 2-S-triphenylmethyl ethers (15 and 29) were directly oxidized to sugar 2-C-sulfonic acids by using oxone (2KHSO(5), KHSO4, K2SO4)- Compounds (21, 23, 32, and 35) are the first representatives of secondary sugar C-sulfonic acids.

  DOI：

  10.1021/ol0353518
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-yl ester 在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 Methanesulfonic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  A General Method for the Synthesis of Sugar 2-C-Sulfonic Acids by 1 → 2 Arylthio Group Migration in Acid-Sensitive Thioglycosides.¹ Direct Transformation of Thiotrityl Ethers into C-Sulfonic Acids

  摘要：

  Fully protected triphenylmethyl 2-O-mesyl-1-thio-beta-D-gluco- (14) and -alpha-D-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 --> 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-alpha-D-manno- (15) and -beta-D-glucopyranoside (29), respectively, using NaOCH3 as nucleophile. The 2-S-triphenylmethyl ethers (15 and 29) were directly oxidized to sugar 2-C-sulfonic acids by using oxone (2KHSO(5), KHSO4, K2SO4)- Compounds (21, 23, 32, and 35) are the first representatives of secondary sugar C-sulfonic acids.

  DOI：

  10.1021/ol0353518