methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-galactopyranoside | 204321-88-0

• 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: methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-galactopyranoside
• 英文别名: [(2R,3R,4R,5R,6S)-5-benzamido-4-benzoyloxy-6-methoxy-3-sulfanyloxan-2-yl]methyl benzoate
• CAS: 204321-88-0
• 化学式: C₂₈H₂₇NO₇S
• 分子量: 521.591
• InChiKey: IFQQAQWKYFTOFP-GJNSLUDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以94%的产率得到N-((2S,3R,4R,5R,6R)-4-Hydroxy-6-hydroxymethyl-5-mercapto-2-methoxy-tetrahydro-pyran-3-yl)-benzamide
  参考文献：
  名称：

  4-Thiopyranoside and 4-thiofuranoside derivatives of d-galactosamine

  摘要：

  Methyl 2-benzamido-2-deoxy-4-thio-alpha-D-galactopyranoside (7) was prepared in different ways starting from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (1). A 4,6-epidithiogalactopyranoside was obtained from the 4-O-mesyl derivative of 1. The transformations of 7 into 2-benzamido-2-deoxy-4-thio-D-galactofuran and into the corresponding methyl alpha- and beta-4-thio-D-galactofuranosides are reported. The T-2(3) conformation is proposed for the alpha anomers of the prepared furanoid compounds. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00218-8
• 作为产物：
  描述：

  methyl 2-benzamido-3,6-di-O-benzoyl-4-O-(4-bromobenzenesulfonyl)-2-deoxy-α-D-glucopyranoside 在 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-galactopyranoside
  参考文献：
  名称：

  4-Thiopyranoside and 4-thiofuranoside derivatives of d-galactosamine

  摘要：

  Methyl 2-benzamido-2-deoxy-4-thio-alpha-D-galactopyranoside (7) was prepared in different ways starting from methyl 2-benzamido-3,6-di-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (1). A 4,6-epidithiogalactopyranoside was obtained from the 4-O-mesyl derivative of 1. The transformations of 7 into 2-benzamido-2-deoxy-4-thio-D-galactofuran and into the corresponding methyl alpha- and beta-4-thio-D-galactofuranosides are reported. The T-2(3) conformation is proposed for the alpha anomers of the prepared furanoid compounds. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)00218-8