ethyl O3,O5,O6-phosphanetriyl-α-D-1-thio-glucofuranoside | 57204-13-4

• 分子结构分类: 有机化合物 - 有机磷化合物 - 亚磷酸三烷基酯
• 英文名称: ethyl O3,O5,O6-phosphanetriyl-α-D-1-thio-glucofuranoside
• 英文别名: (ethyl 1-thio-α-D-glucofuranoside) 3,5,6-phosphite
• CAS: 57204-13-4；250338-25-1
• 化学式: C₈H₁₃O₅PS
• 分子量: 252.228
• InChiKey: YDNLTNRVFDGVLC-AVJYPTNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl O3,O5,O6-phosphanetriyl-α-D-1-thio-glucofuranoside 在 sulfur 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 Isophthalic acid bis-((1R,2R,4R,5R,6S,8S)-4-ethylsulfanyl-8-thioxo-3,7,9,11-tetraoxa-8λ⁵-phospha-tricyclo[6.2.1.0^2,6]undec-5-yl) ester
  参考文献：
  名称：

  Bis- and tris-bicyclophosphites of d-glucofuranoside. Unexpected catalysis of P(III/V)-oxidation by triethylamine

  摘要：

  The synthesis and characterization of several new bicyclophosphites via reactions of (i) ethyl 1-thi-alpha-D-glucofuranoside 3,5,6-phosphite with acid chlorides (phthalic or butylphosphoric), (ii) ethyl 1-thio-alpha-D-glucofuranosicle 3,5,6-phosphite with 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane and (iii) the tetraol system of ethyl 1-thio-alpha-D-glucofuranoside and hexaethyltriamidophosphite are reported. Unusual catalytic transformation of P(III)-compounds into the respective P(V)-spieces under extraordinary mild conditions by reaction with sulfur and selenium in the presence of triethylamine was discovered for the first time. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.102
• 作为产物：
  描述：

  乙基 1-硫代-alpha-D-呋喃葡糖苷 在 六乙基亚磷酸胺 作用下， 反应 5.0h， 以24%的产率得到
  参考文献：
  名称：

  Bis- and tris-bicyclophosphites of d-glucofuranoside. Unexpected catalysis of P(III/V)-oxidation by triethylamine

  摘要：

  The synthesis and characterization of several new bicyclophosphites via reactions of (i) ethyl 1-thi-alpha-D-glucofuranoside 3,5,6-phosphite with acid chlorides (phthalic or butylphosphoric), (ii) ethyl 1-thio-alpha-D-glucofuranosicle 3,5,6-phosphite with 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane and (iii) the tetraol system of ethyl 1-thio-alpha-D-glucofuranoside and hexaethyltriamidophosphite are reported. Unusual catalytic transformation of P(III)-compounds into the respective P(V)-spieces under extraordinary mild conditions by reaction with sulfur and selenium in the presence of triethylamine was discovered for the first time. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.102