(2R,3R,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-tritylsulfanyl-tetrahydro-pyran-3,5-diol | 616238-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-tritylsulfanyl-tetrahydro-pyran-3,5-diol
• CAS: 616238-15-4
• 化学式: C₃₂H₃₂O₅S
• 分子量: 528.669
• InChiKey: GKWHIHRXTIRTMJ-DXKYAHCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-tritylsulfanyl-tetrahydro-pyran-3,5-diol 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 、 silver nitrate 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (4aR,6S,7S,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7-thiol
  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)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-carbamimidoylsulfanyl-tetrahydro-pyran-3-yl ester; hydrobromide 在 sodium methylate 、 sodium carbonate 、 sodium sulfite 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 25.5h， 生成 (2R,3R,4S,5R,6S)-4-Benzyloxy-2-hydroxymethyl-6-tritylsulfanyl-tetrahydro-pyran-3,5-diol
  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