Diethyl (3R,4R,5R)-3,4:5,6-di-O-isopropylidene-3,4,5,6-tetrahydroxy-1-hexene-1-phosphonate | 33805-16-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Diethyl (3R,4R,5R)-3,4:5,6-di-O-isopropylidene-3,4,5,6-tetrahydroxy-1-hexene-1-phosphonate
• 英文别名: (4R,5S)-4-[(E)-2-diethoxyphosphorylethenyl]-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 33805-16-2
• 化学式: C₁₆H₂₉O₇P
• 分子量: 364.376
• InChiKey: HQOYBSDVWMXXCU-JIMGKXMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl (3R,4R,5R)-3,4:5,6-di-O-isopropylidene-3,4,5,6-tetrahydroxy-1-hexene-1-phosphonate 在 盐酸 作用下， 生成 1,2-Didesoxy-D-arabino-trans-hex-1-enit-phosphonsaeure-diethylester
  参考文献：
  名称：

  Paulsen,H.; Bartsch,W., Chemische Berichte, 1975, vol. 108, p. 1732 - 1744

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,3R,4R)-2,3:4,5-Di-O-isopropylidene-2,3,4,5-tetrahydroxy-pentanoic acid 在 N-甲基吗啉 、 间氯过氧苯甲酸 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 Diethyl (3R,4R,5R)-3,4:5,6-di-O-isopropylidene-3,4,5,6-tetrahydroxy-1-hexene-1-phosphonate
  参考文献：
  名称：

  From carbohydrates to carbocycles: radical routes via Tellurium derivatives

  摘要：

  D-Ribose was transformed to its protected tosylate 15, followed by a Wittig-reaction to give 16 as a 3:1 mixture of the corresponding Z and E isomers. This mixture was then transformed to the anisyltelluride 17 and the latter cyclized in a radical exchange reaction to a mixture of the carbocycles 18a and 18b (in a 17:2 ratio). The major product 18a was then transformed to various chiral cyclopentane derivatives including the cyclopentenone-derivative 23. Various other carbohydrate-based approaches have also been explored.

  DOI：

  10.1016/s0040-4020(01)85616-7

文献信息

• Concise Synthesis of<i>P</i>-Glycosyl Alkenylphosphonates and<i>P,C</i>-di and<i>P,P,C</i>tri-Glycosyl Phosphonates
  作者：Claude Grison、Hicham Chibli

  DOI：10.1080/07328300802638472

  日期：2009.1.30

  A direct access to P-glycosyl-, P, P-di-glycosyl alkenylphosphonates and P, C-glycosyl phosphonates is described. The method involves the Horner reaction of an anion derived from P-monoglycosyl and P1, P'-diglycosyl methylenediphosphonates either on the exocyclic aldehyde group of carbohydrates or on the masked aldehydic form of the furanose hemiacetals. In this last case, the carbonyl olefination, followed by an intramolecular cyclization, leads to P,C-di and P,P,C-triglycosyl phosphonates.
• Paulsen,H.; Bartsch,W., Chemische Berichte, 1975, vol. 108, p. 1745 - 1755
  作者：Paulsen,H.、Bartsch,W.

  DOI：——

  日期：——