methyl (methyl 9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 361206-63-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-6-[(1R,2R)-3-benzamido-1,2-dihydroxypropyl]-4,5-dihydroxy-2-methoxyoxane-2-carboxylate
• CAS: 361206-63-5
• 化学式: C₁₈H₂₅NO₉
• 分子量: 399.398
• InChiKey: DRWNKBFTHBTIKS-JIOXDANUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl (methyl 9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以92%的产率得到methyl (methyl 4,5,7,8-tetra-O-acetyl-9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER

  摘要：

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.

  DOI：

  10.1081/car-100103960
• 作为产物：
  描述：

  methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 palladium on activated charcoal 叠氮基三甲基硅烷 、 偶氮二甲酸二异丙酯 、 氢气 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -70.0~20.0 ℃ 、344.74 kPa 条件下， 反应 156.58h， 生成 methyl (methyl 9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER

  摘要：

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.

  DOI：

  10.1081/car-100103960

文献信息

• THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER
  作者：Adele K. Norton、Gaik B. Kok、Mark von Itzstein

  DOI：10.1081/car-100103960

  日期：2001.3.31

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.