methyl 2,3,4-tri-O-benzyl-6-O-(2'-hydroxypropyl)-α-D-glucopyranoside | 189240-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(2'-hydroxypropyl)-α-D-glucopyranoside
• CAS: 189240-76-4
• 化学式: C₃₁H₃₈O₇
• 分子量: 522.639
• InChiKey: OTLAZJPNFXZASO-WHANNZITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(2'-hydroxypropyl)-α-D-glucopyranoside 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到methyl 6-O-(2'-hydroxypropyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of Methyl 2-O-, 3-O- and 6-O-(2′-Hydroxypropyl)-α-D-Glucopyranosides¹

  摘要：

  Methyl 6-O-, 3-O- and 2-O-(2'-hydroxypropyl)-alpha-D-glucopyranosides (4, 8, and 12) were synthesized starting from methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside (1), methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (5), and methyl 3-O-benzyl-4,6-O-benzylidene-D-glucopyranoside (9), respectively. Overall yields were 88%, 6% and 26% of 4, 8 and 12, respectively, with the 2-ether (12) being crystalline and the 3-ether (8) a single diastereomer.

  DOI：

  10.1080/07328309708006517
• 作为产物：
  描述：

  1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.83h， 以74%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(2'-hydroxypropyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of Methyl 2-O-, 3-O- and 6-O-(2′-Hydroxypropyl)-α-D-Glucopyranosides¹

  摘要：

  Methyl 6-O-, 3-O- and 2-O-(2'-hydroxypropyl)-alpha-D-glucopyranosides (4, 8, and 12) were synthesized starting from methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside (1), methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (5), and methyl 3-O-benzyl-4,6-O-benzylidene-D-glucopyranoside (9), respectively. Overall yields were 88%, 6% and 26% of 4, 8 and 12, respectively, with the 2-ether (12) being crystalline and the 3-ether (8) a single diastereomer.

  DOI：

  10.1080/07328309708006517