methyl (phenyl 3-deoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate | 243866-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 3-deoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-4,5-dihydroxy-2-phenylsulfanyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 243866-35-5
• 化学式: C₁₆H₂₂O₈S
• 分子量: 374.412
• InChiKey: WKHZLXPAYFFUPW-RYQQKAPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 3-deoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 吡啶 、 咪唑 、 Dowex 50W-X₈ (H⁺ form) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 16.0h， 生成 methyl (phenyl 7-O-benzoyl-4-O-t-butyldimethylsilyl-3-deoxy-8,9-O-isopropylidene-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Selective Protecting Method for the Individual Hydroxyl Groups of Kdn

  摘要：

  Selective protection for the individual hydroxyl groups of methyl (phenyl 3-deoxy2-thio-beta-D-glycero-D-galacto-2-nonulopyranodis)onate (2) was examined. The 4-, 5-, and 7-hydroxyl groups of methyl (phenyl 3-deoxy-8,9-O-isopropylidene-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (3) were found selectively to be protected by t-butyldimethylsilyl, methoxymethyl, and benzoyl groups, respectively. In order to obtain the 8- and 9-hydroxyl derivatives selectively, methyl (phenyl 4,5,7-tri-O-acetyl-9-O-t-butyldimethylsilyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (12) and methyl (phenyl 4,5,7,8-tetra-O-benzyl-9-O-triphenylmethyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (19) were prepared in moderate yields.

  DOI：

  10.1080/07328309908544026
• 作为产物：
  描述：

  methyl (phenyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以94%的产率得到methyl (phenyl 3-deoxy-2-thio-β-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Selective Protecting Method for the Individual Hydroxyl Groups of Kdn

  摘要：

  Selective protection for the individual hydroxyl groups of methyl (phenyl 3-deoxy2-thio-beta-D-glycero-D-galacto-2-nonulopyranodis)onate (2) was examined. The 4-, 5-, and 7-hydroxyl groups of methyl (phenyl 3-deoxy-8,9-O-isopropylidene-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (3) were found selectively to be protected by t-butyldimethylsilyl, methoxymethyl, and benzoyl groups, respectively. In order to obtain the 8- and 9-hydroxyl derivatives selectively, methyl (phenyl 4,5,7-tri-O-acetyl-9-O-t-butyldimethylsilyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (12) and methyl (phenyl 4,5,7,8-tetra-O-benzyl-9-O-triphenylmethyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (19) were prepared in moderate yields.

  DOI：

  10.1080/07328309908544026

文献信息

• Selective Protecting Method for the Individual Hydroxyl Groups of Kdn
  作者：Shoji Akai、Takahiro Nakagawa、Yasuhiro Kajihara、Ken-ichi Sato

  DOI：10.1080/07328309908544026

  日期：1999.1

  Selective protection for the individual hydroxyl groups of methyl (phenyl 3-deoxy2-thio-beta-D-glycero-D-galacto-2-nonulopyranodis)onate (2) was examined. The 4-, 5-, and 7-hydroxyl groups of methyl (phenyl 3-deoxy-8,9-O-isopropylidene-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (3) were found selectively to be protected by t-butyldimethylsilyl, methoxymethyl, and benzoyl groups, respectively. In order to obtain the 8- and 9-hydroxyl derivatives selectively, methyl (phenyl 4,5,7-tri-O-acetyl-9-O-t-butyldimethylsilyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (12) and methyl (phenyl 4,5,7,8-tetra-O-benzyl-9-O-triphenylmethyl-3-deoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate (19) were prepared in moderate yields.