(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-ol | 616238-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-ol
• CAS: 616238-06-3
• 化学式: C₃₅H₃₈O₆S
• 分子量: 586.749
• InChiKey: ISSGCFUXTRZINX-JSMUHSIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-ol 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以87%的产率得到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
• 作为产物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide 在 sodium methylate 、 sodium carbonate 、 sodium sulfite 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 40.5h， 生成 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-benzylsulfanyl)-tetrahydro-pyran-3-ol
  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