2-O-[(4-methyl)phenylsulfonyl]-1,6-anhydro-3,4-dideoxy-β-D-threo-hexopyranose | 39682-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-O-[(4-methyl)phenylsulfonyl]-1,6-anhydro-3,4-dideoxy-β-D-threo-hexopyranose
• 英文别名: 1.6-Anhydro-3.4-dideoxy-2-O-p-toluolsulfonyl-β-D-threo-hexopyranose；[(1S,4S,5R)-6,8-dioxabicyclo[3.2.1]octan-4-yl] 4-methylbenzenesulfonate
• CAS: 39682-52-5
• 化学式: C₁₃H₁₆O₅S
• 分子量: 284.333
• InChiKey: QSVFNZDVKKFZGC-WCFLWFBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-O-[(4-methyl)phenylsulfonyl]-1,6-anhydro-3,4-dideoxy-β-D-threo-hexopyranose 、 sodium benzoate 生成 1,6-anhydro-3-O-benzoyl-2,4-dideoxy-β-D-erythro-hexopyranoside
  参考文献：
  名称：

  DAVID, C.;GESSON, J. P.;JACQUESY, J. C., TETRAHEDRON LETT., 30,(1989) N4, C. 6015-6018

  摘要：

  DOI：
• 作为产物：
  描述：

  二氢左旋葡萄糖酮 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 2-O-[(4-methyl)phenylsulfonyl]-1,6-anhydro-3,4-dideoxy-β-D-threo-hexopyranose
  参考文献：
  名称：

  Synthesis of Methylene-Expanded 2‘,3‘-Dideoxyribonucleosides

  摘要：

  A method for the preparation of methylene-expanded 2',3'-dideoxyribonucleosides is reported. The very inexpensive starting material levoglucosenone 8 was converted into the known mixture of alcohols 12ab which were converted into the required silyl ether alcohol 26 in six steps via either of two routes. The first involved a one-step acetylation and opening of the anhydro sugar bridge to give the triacetates 20ab which were reduced with triethylsilane and silyl triflate to afford the diacetates 21ab, both of which gave 26 after further functional group conversions. The second route entailed a simple acetylation of 12ab followed by reduction with triethylsilane and silyl triflate to give the monoacetates 19ab, both converted via straightforward chemistry into 26. Mesylation of the alcohol of 26 furnished the mesylate 27. Alkylation of adenine with the mesylate 27 afforded the silyl ether 28 which was deprotected to give the desired modified dideoxy nucleoside 7a. Alkylation of 2,6-diaminopurine 38 with the mesylate gave the protected diaminopurine nucleoside 39. Upon acetylation, it produced a mixture of di- and monoacetates 40-41, the latter of which was transformed into the desired guanosine analogue 7e. Thus, two new nucleoside analogues 7ae were prepared from levoglucosenone 8.

  DOI：

  10.1021/jo980436l

文献信息

• Synthesis of Purpurosamine TBDMS Ether from Cyrene™
  作者：L. Kh. Faizullina、Yu. S. Galimova、F. A. Valeev

  DOI：10.1134/s1070428021100092

  日期：2021.10

  Abstract A procedure has been developed for the synthesis of purpurosamine tert-butyl(dimethyl)silyl ether starting from dihydrolevoglucosenone (cyrene™) via successive reduction of the keto group, tosylation, cleavage of the 1,6-anhydro bridge, mesylation of the primary hydroxy group, TBDMS protection of the acetal moiety, and nucleophilic substitution in liquid ammonia in a sealed ampule at 100°C

  摘要 已经开发出一种从二氢左旋葡萄糖烯酮 (cyrene ™ )开始，通过酮基的连续还原、甲苯磺酰化、1,6-脱水桥的裂解、伯羟基的甲磺酰化合成 purpurosamine叔丁基（二甲基）甲硅烷基醚的方法组，缩醛部分的 TBDMS 保护，以及在 100°C 密封安瓿中液氨中的亲核取代。
• DAVID, C.;GESSON, J. P.;JACQUESY, J. C., TETRAHEDRON LETT., 30,(1989) N4, C. 6015-6018
  作者：DAVID, C.、GESSON, J. P.、JACQUESY, J. C.

  DOI：——

  日期：——
• Synthesis of Methylene-Expanded 2‘,3‘-Dideoxyribonucleosides
  作者：Michael E. Jung、Mehrak Kiankarimi

  DOI：10.1021/jo980436l

  日期：1998.11.1

  A method for the preparation of methylene-expanded 2',3'-dideoxyribonucleosides is reported. The very inexpensive starting material levoglucosenone 8 was converted into the known mixture of alcohols 12ab which were converted into the required silyl ether alcohol 26 in six steps via either of two routes. The first involved a one-step acetylation and opening of the anhydro sugar bridge to give the triacetates 20ab which were reduced with triethylsilane and silyl triflate to afford the diacetates 21ab, both of which gave 26 after further functional group conversions. The second route entailed a simple acetylation of 12ab followed by reduction with triethylsilane and silyl triflate to give the monoacetates 19ab, both converted via straightforward chemistry into 26. Mesylation of the alcohol of 26 furnished the mesylate 27. Alkylation of adenine with the mesylate 27 afforded the silyl ether 28 which was deprotected to give the desired modified dideoxy nucleoside 7a. Alkylation of 2,6-diaminopurine 38 with the mesylate gave the protected diaminopurine nucleoside 39. Upon acetylation, it produced a mixture of di- and monoacetates 40-41, the latter of which was transformed into the desired guanosine analogue 7e. Thus, two new nucleoside analogues 7ae were prepared from levoglucosenone 8.