Toluene-4-sulfonic acid (3aR,4S,6S,7S,7aR)-7-hydroxy-6-methoxy-3,7a-dimethyl-2-oxo-hexahydro-pyrano[3,4-d]oxazol-4-ylmethyl ester | 92840-92-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Toluene-4-sulfonic acid (3aR,4S,6S,7S,7aR)-7-hydroxy-6-methoxy-3,7a-dimethyl-2-oxo-hexahydro-pyrano[3,4-d]oxazol-4-ylmethyl ester
• CAS: 92840-92-1
• 化学式: C₁₇H₂₃NO₈S
• 分子量: 401.438
• InChiKey: FKIXRKIELGBWDT-WVCIDPQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  111.6
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (3aR,4S,6S,7S,7aR)-7-hydroxy-6-methoxy-3,7a-dimethyl-2-oxo-hexahydro-pyrano[3,4-d]oxazol-4-ylmethyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以83%的产率得到3-N-methyl-(methyl 4,6-dideoxy-6-iodo-3-C-methyl-α-D-altropyranosido)-<3,4-d>-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A synthesis of methyl 4,6-dideoxy-3-C-methyl-4-(N-methylacetamido)-α-d-altropyranoside, the 3-epimer of (methyl N-acetylsibirosaminide)

  摘要：

  The oxirane ring of 1,6:3,4-dianhydro-beta-D-talopyranose reacted at C-4 with methylamine, and the product, further processed gave a 3-deoxy-C-3-methylene derivative. Iodonium ion-induced cyclisation led to an iodooxazolidinone, and deiodination, followed by hydrolysis and N-acetylation, to the title compound.

  DOI：

  10.1016/0008-6215(84)85274-x
• 作为产物：
  描述：

  methyl-3-N-(1,2,6-tri-O-acetyl-4-deoxy-3-C-methyl-α,β-D-altropyrano)-<3,4-d>-1,3-oxazolidin-2-one 在 吡啶 、 Dowex 50 (H+) resin 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.75h， 生成 Toluene-4-sulfonic acid (3aR,4S,6S,7S,7aR)-7-hydroxy-6-methoxy-3,7a-dimethyl-2-oxo-hexahydro-pyrano[3,4-d]oxazol-4-ylmethyl ester
  参考文献：
  名称：

  A synthesis of methyl 4,6-dideoxy-3-C-methyl-4-(N-methylacetamido)-α-d-altropyranoside, the 3-epimer of (methyl N-acetylsibirosaminide)

  摘要：

  The oxirane ring of 1,6:3,4-dianhydro-beta-D-talopyranose reacted at C-4 with methylamine, and the product, further processed gave a 3-deoxy-C-3-methylene derivative. Iodonium ion-induced cyclisation led to an iodooxazolidinone, and deiodination, followed by hydrolysis and N-acetylation, to the title compound.

  DOI：

  10.1016/0008-6215(84)85274-x