[(4aR,6R,7S,8S,8aR)-2,2-dimethyl-8-phenylmethoxy-6-tritylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate | 616238-34-7

• 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: [(4aR,6R,7S,8S,8aR)-2,2-dimethyl-8-phenylmethoxy-6-tritylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate
• CAS: 616238-34-7
• 化学式: C₃₆H₃₈O₇S₂
• 分子量: 646.826
• InChiKey: AFIOSMBVZCCTDL-ZYSDIQSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  sodium methylate 、 [(4aR,6R,7S,8S,8aR)-2,2-dimethyl-8-phenylmethoxy-6-tritylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以49%的产率得到methyl 3-O-benzyl-4,6-O-isopropylidene-2-deoxy-2-thio-2-S-trityl-β-D-glucopyranoside
  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：

  三苯甲硫醇 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 [(4aR,6R,7S,8S,8aR)-2,2-dimethyl-8-phenylmethoxy-6-tritylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate
  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

文献信息

• A General Method for the Synthesis of Sugar 2-<i>C</i>-Sulfonic Acids by 1 → 2 Arylthio Group Migration in Acid-Sensitive Thioglycosides.¹ Direct Transformation of Thiotrityl Ethers into <i>C</i>-Sulfonic Acids
  作者：András Lipták、Ferenc Sajtos、Lóránt Jánossy、Diethmar Gehle、László Szilágyi

  DOI：10.1021/ol0353518

  日期：2003.10.1

  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.