methyl 3-O-benzyl-2-deoxy-β-D-glycero-pentopyranosid-4-ulose | 1007301-84-9

• 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 3-O-benzyl-2-deoxy-β-D-glycero-pentopyranosid-4-ulose
• 英文别名: (4S,6R)-6-methoxy-4-phenylmethoxyoxan-3-one
• CAS: 1007301-84-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: GUEZAZLBCCCCKT-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-2-deoxy-β-D-glycero-pentopyranosid-4-ulose 、 亚磷酸二甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 1.0h， 生成 methyl (4R)-3-O-benzyl-2-deoxy-4-C-dimethoxyphosphinoyl-β-D-glycero-pentopyranoside 、 methyl (4S)-3-O-benzyl-2-deoxy-4-C-dimethoxyphosphinoyl-β-D-glycero-pentopyranoside
  参考文献：
  名称：

  Improved Syntheses of D-Ribo- and 2-Deoxy-D-ribofuranose Phospho Sugars from Methyl b-D-Ribopyranoside

  摘要：

  Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-beta-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-beta-D-erythro-pentopyranoside (20) were efficiently prepared respectively from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside (7a) and its 3,4-O-isopropylidene isomer (7b) in appreciably improved total yields compared with those via previously reported routes. Compounds (12a, 20) were led to D-ribofuranose and 2-deoxy-D-ribofuranose phospho sugars (4, 5).

  DOI：

  10.3987/com-07-s(u)34
• 作为产物：
  描述：

  Methyl 3-benzyl-2-deoxy-β-D-erythro-pentopyranoside 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以90%的产率得到methyl 3-O-benzyl-2-deoxy-β-D-glycero-pentopyranosid-4-ulose
  参考文献：
  名称：

  Improved Syntheses of D-Ribo- and 2-Deoxy-D-ribofuranose Phospho Sugars from Methyl b-D-Ribopyranoside

  摘要：

  Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-beta-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-beta-D-erythro-pentopyranoside (20) were efficiently prepared respectively from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside (7a) and its 3,4-O-isopropylidene isomer (7b) in appreciably improved total yields compared with those via previously reported routes. Compounds (12a, 20) were led to D-ribofuranose and 2-deoxy-D-ribofuranose phospho sugars (4, 5).

  DOI：

  10.3987/com-07-s(u)34

文献信息

• Improved Syntheses of D-Ribo- and 2-Deoxy-D-ribofuranose Phospho Sugars from Methyl b-D-Ribopyranoside
  作者：Tadashi Hanaya、Yuko Koga、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.3987/com-07-s(u)34

  日期：——

  Methyl 4-deoxy-4-dimethoxyphosphinoyl-2,3-O-isopropylidene-beta-D-ribopyranoside (12a) and methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-beta-D-erythro-pentopyranoside (20) were efficiently prepared respectively from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside (7a) and its 3,4-O-isopropylidene isomer (7b) in appreciably improved total yields compared with those via previously reported routes. Compounds (12a, 20) were led to D-ribofuranose and 2-deoxy-D-ribofuranose phospho sugars (4, 5).