Methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-β-D-erythro-pentopyranoside | 140422-29-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: Methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-β-D-erythro-pentopyranoside
• 英文别名: (2R,4S,5R)-5-dimethoxyphosphoryl-2-methoxyoxan-4-ol
• CAS: 140422-29-3
• 化学式: C₈H₁₇O₆P
• 分子量: 240.193
• InChiKey: JJNQDDFYTOIMLY-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-β-D-erythro-pentopyranoside 在 红铝 、 盐酸 、 双氧水 作用下， 以 甲苯 、 水 、 异丙醇 为溶剂， 反应 14.0h， 生成 2,4-dideoxy-4-hydroxyphosphinyl-D-erythro-pentofuranose
  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：

  (5RS)-3,5-Dideoxy-5-dimethoxyphosphinoyl-α,β-D-erythro-hexofuranose 在 sodium periodate 、 Amberlite IR-120 (H⁽¹⁺⁾) 作用下， 以 水 为溶剂， 反应 12.0h， 生成 Methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-β-D-erythro-pentopyranoside
  参考文献：
  名称：

  Hanaya, Tadashi; Noguchi, Ayashi; Armour, Margaret-Ann, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 295 - 301

  摘要：

  DOI：

文献信息

• A New Route for Preparation of 2-Deoxy-D-ribofuranose Phospho Sugar
  作者：Tadashi Hanaya、Hiroyuki Tsukui、Naomi Igi、Ayashi Noguchi、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(k)28

  日期：——

  The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tertbutyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxyphosphinoyl-2,4-O-ethylidene-D-erythritol (13a). Elongation of carbon skeleton of the D-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-alpha,beta-D-erythropentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route.
• An efficient synthesis of 2,4-dideoxy-4-hydroxyphosphinyl-d-erythro-pentofuranose
  作者：Tadashi Hanaya、Ayashi Noguchi、Hiroshi Yamamoto

  DOI：10.1016/0008-6215(91)80173-k

  日期：1991.1
• HANAYA, TADASHI;NOGUCHI, AYASHI;YAMAMOTO, HIROSHI, CARBOHYDR. RES., 209,(1991) C9-C12
  作者：HANAYA, TADASHI、NOGUCHI, AYASHI、YAMAMOTO, HIROSHI

  DOI：——

  日期：——
• 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).
• Hanaya, Tadashi; Noguchi, Ayashi; Armour, Margaret-Ann, Journal of the Chemical Society. Perkin transactions I, 1992, # 2, p. 295 - 301
  作者：Hanaya, Tadashi、Noguchi, Ayashi、Armour, Margaret-Ann、Hogg, Alan M.、Yamamoto, Hiroshi

  DOI：——

  日期：——