4-deoxy-4-(hydroxyphosphinyl)-α,β-D-ribofuranoside | 121682-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 4-deoxy-4-(hydroxyphosphinyl)-α,β-D-ribofuranoside
• 英文别名: 4-deoxy-4-(hydroxyphosphinyl)-D-ribofuranose；4-deoxy-4-hydroxyphosphonoyl-D-ribofuranose；(3R,4S,5R)-1-hydroxy-5-(hydroxymethyl)-1-oxo-1lambda5-phospholane-2,3,4-triol；(3R,4S,5R)-1-hydroxy-5-(hydroxymethyl)-1-oxo-1λ5-phospholane-2,3,4-triol
• CAS: 121682-78-8；121785-05-5
• 化学式: C₅H₁₁O₆P
• 分子量: 198.112
• InChiKey: VDHKPQONGDLMNW-SOOFDHNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-deoxy-4-(hydroxyphosphinyl)-α,β-D-ribofuranoside 生成 [(1S,2R,3S,4R,5R)-3,4-diacetyloxy-1,5-dimethoxy-1-oxo-1λ5-phospholan-2-yl]methyl acetate
  参考文献：
  名称：

  YAMAMOTO, HIROSHI;HANAYA, TADASHI;KAWAMOTO, HEIZAN;INOKAWA, SABURO, CHEM. LETT.,(1989) N, C. 121-124

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-β-D-ribopyranoside 在 盐酸 、 sodium tetrahydroborate 、 三氟甲磺酸 、 3 A molecular sieve 、 双氧水 、 红铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 29.0h， 生成 4-deoxy-4-(hydroxyphosphinyl)-α,β-D-ribofuranoside
  参考文献：
  名称：

  An Efficient Synthesis of 4-Deoxy-4-(hydroxyphosphinyl)-D-ribofuranoses. The First D-Ribofuranose Analogues Having Hydroxyphosphinyl Group in the Hemiacetal Ring

  摘要：

  将甲基 2,3-O-异亚丙基-β-d-吡喃核糖苷（分 4 步）转化为甲基 4-脱氧-4-[（二甲氧基）膦酰基]-2,3-O-异亚丙基-β-d-吡喃核糖苷（10a，总收率 30%）。标题化合物很容易从 10a 中衍生出来，并表征为 4-脱氧-4-（甲氧基膦酰基）四乙酸酯。

  DOI：

  10.1246/cl.1989.121

文献信息

• Synthesis and Structural Analysis of 4-Deoxy-4-(hydroxyphosphinyl and phenylphosphinyl)-D-ribofuranoses
  作者：Tadashi Hanaya、Hiroshi Yamamoto

  DOI：10.1246/bcsj.62.2320

  日期：1989.7

  e gave efficiently (in 4 steps) methyl 4-deoxy-4-[dimethoxyphosphinyl and (methoxy)phenylphosphinyl]-2,3-O-isopropylidene-β-D-ribopyranosides (ca. 30% overall yield). These were led (in 2–3 steps) to the title compounds and then converted into 1,2,3,5-tetra-O-acetyl-4-deoxy-4-(methoxyphosphinyl and phenylphosphinyl)-D-ribofuranoses, whose structures and 3T2 (and 2T3) conformations were established

  甲基 2,3-O-isopropylidene-β-D-ribopyranosides 有效地（分 4 个步骤）得到甲基 4-deoxy-4-[二甲氧基膦基和（甲氧基）苯基膦基]-2,3-O-isopropylidene-β-D-ribopyranosides （大约 30% 的总收率）。这些被引导（分 2-3 步）得到标题化合物，然后转化为 1,2,3,5-四-O-乙酰基-4-脱氧-4-（甲氧基膦基和苯基膦基）-D-呋喃核糖，其结构和 3T2（和 2T3）构象是通过光谱法建立的。
• 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).
• YAMAMOTO, HIROSHI;HANAYA, TADASHI;KAWAMOTO, HEIZAN;INOKAWA, SABURO, CHEM. LETT.,(1989) N, C. 121-124
  作者：YAMAMOTO, HIROSHI、HANAYA, TADASHI、KAWAMOTO, HEIZAN、INOKAWA, SABURO

  DOI：——

  日期：——
• An Efficient Synthesis of 4-Deoxy-4-(hydroxyphosphinyl)-D-ribofuranoses. The First D-Ribofuranose Analogues Having Hydroxyphosphinyl Group in the Hemiacetal Ring
  作者：Hiroshi Yamamoto、Tadashi Hanaya、Heizan Kawamoto、Saburo Inokawa

  DOI：10.1246/cl.1989.121

  日期：1989.1

  Methyl 2,3-O-isopropylidene-β-d-ribopyranoside was converted (in 4 steps) into methyl 4-deoxy-4-[(dimethoxy)phosphinyl]-2,3-O-isopropylidene-β-d-ribopyranoside (10a, 30% overall yield). The title compounds were readily derived from 10a and characterized as the 4-deoxy-4-(methoxyphosphinyl) tetraacetates.

  将甲基 2,3-O-异亚丙基-β-d-吡喃核糖苷（分 4 步）转化为甲基 4-脱氧-4-[（二甲氧基）膦酰基]-2,3-O-异亚丙基-β-d-吡喃核糖苷（10a，总收率 30%）。标题化合物很容易从 10a 中衍生出来，并表征为 4-脱氧-4-（甲氧基膦酰基）四乙酸酯。