(2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-(naphthalen-2-ylmethylsulfanyl)-tetrahydro-pyran | 616238-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-(naphthalen-2-ylmethylsulfanyl)-tetrahydro-pyran
• CAS: 616238-12-1
• 化学式: C₃₉H₄₀O₅S
• 分子量: 620.81
• InChiKey: GDIVECGRKOTSMB-QRBPUMSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-(naphthalen-2-ylmethylsulfanyl)-tetrahydro-pyran 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以20%的产率得到methyl 4-O-acetyl-2-S-acetyl-3,6-di-O-benzyl-2-deoxy-2-thio-α-D-mannopyranoside
  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：

  在 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 4.0h， 生成 (2R,3R,4S,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-(naphthalen-2-ylmethylsulfanyl)-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