1,2,3,4-tetra-O-acetyl-4-deoxy-4<(R)-methoxyphosphynyl>-α-D-ribofuranoside | 121785-06-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,3,4-tetra-O-acetyl-4-deoxy-4<(R)-methoxyphosphynyl>-α-D-ribofuranoside
• 英文别名: 1,2,3,5-tetra-O-acetyl-4-deoxy-4-<(R)-methoxyphosphinyl>-α-D-ribofuranose；1,2,3,5-tetra-O-acetyl-4-deoxy-4-[(R)-methoxyphosphonoyl]-α-D-ribofuranose；1,2,3,5-tetra-O-acetyl-4-deoxy-4-((R)-methoxyphosphinyl)-α-D-ribofuranose
• CAS: 121785-06-6
• 化学式: C₁₄H₂₁O₁₀P
• 分子量: 380.288
• InChiKey: QFSRVQZCYTWHML-BGZGBZMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 双氧水 、 红铝 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 苯 为溶剂， 反应 14.0h， 生成 1,2,3,4-tetra-O-acetyl-4-deoxy-4<(R)-methoxyphosphynyl>-α-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).