[ethyl 2-O-(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-yl)-1-thio-α-D-glucofuranoside] 3,5,6-phosphite | 250338-28-4

• 分子结构分类: 有机化合物 - 有机磷化合物
• 英文名称: [ethyl 2-O-(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-yl)-1-thio-α-D-glucofuranoside] 3,5,6-phosphite
• CAS: 250338-28-4
• 化学式: C₁₃H₂₂O₇P₂S
• 分子量: 384.327
• InChiKey: ZAOJUFPCUARQKI-CYLSLRBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [ethyl 2-O-(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-yl)-1-thio-α-D-glucofuranoside] 3,5,6-phosphite 在 sulfur 作用下， 以 苯 为溶剂， 反应 12.0h， 以67%的产率得到[ethyl 2-O-(5,5-dimethyl-2-sulfide-1,3,2-dioxaphosphorinan-2-yl)-1-thio-α-D-glucofuranoside] 3,5,6-phosphite
  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：

  ethyl O3,O5,O6-phosphanetriyl-α-D-1-thio-glucofuranoside 、 2-氯-5,5-二甲基-1,3,2-二氧磷杂环己烷 在 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以60%的产率得到[ethyl 2-O-(5,5-dimethyl-1,3,2-dioxaphosphorinane-2-yl)-1-thio-α-D-glucofuranoside] 3,5,6-phosphite
  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