6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-talopyranose | 867258-88-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-talopyranose
• CAS: 867258-88-6
• 化学式: C₂₇H₄₀O₇Si
• 分子量: 504.696
• InChiKey: CWMCOXCMCHWGJZ-VBSLVYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  35.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  86.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-talopyranose 在 原乙酸三甲酯 、 三甲基溴硅烷 、 三氟甲磺酸 、 4 A molecular sieve 、 碘 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 114.25h， 生成 2-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-talopyranose
  参考文献：
  名称：

  Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-β-d-altropyranose derivatives

  摘要：

  We have developed practical synthetic routes to enantiopure D- and L-carba-beta-altrose derivatives and all the possible stereoisomers via their divergent stereoconversions. Carba-beta-D-altrose was prepared from 3-cyclohexene-l-carboxylic acid and converted to carba-beta-D-mannose, carba-beta-D-idose, and carba-beta-D-talose derivatives via regio- and stereoselective oxidation/reduction of 3-OH and/or 4-OH. The four carbasugar stereoisomers were then transformed to the remaining 12 carbasugar stereoisomers and their 1,2-epoxides by regio- and stereoselective manipulation of hydroxyl groups in C1 and C2, which includes oxidation/reduction, Mitsunobu's reaction, olefination/dihydroxylation, and epoxidation/ring-opening protocols. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.010
• 作为产物：
  描述：

  Benzoic acid (1S,2S,3S,4R,6R)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-3,4-bis-methoxymethoxy-cyclohexyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以94.8%的产率得到6-O-(tert-butyldiphenyl)silyl-1,2-di-O-(methoxymethyl)-5a-carba-β-D-talopyranose
  参考文献：
  名称：

  Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-β-d-altropyranose derivatives

  摘要：

  We have developed practical synthetic routes to enantiopure D- and L-carba-beta-altrose derivatives and all the possible stereoisomers via their divergent stereoconversions. Carba-beta-D-altrose was prepared from 3-cyclohexene-l-carboxylic acid and converted to carba-beta-D-mannose, carba-beta-D-idose, and carba-beta-D-talose derivatives via regio- and stereoselective oxidation/reduction of 3-OH and/or 4-OH. The four carbasugar stereoisomers were then transformed to the remaining 12 carbasugar stereoisomers and their 1,2-epoxides by regio- and stereoselective manipulation of hydroxyl groups in C1 and C2, which includes oxidation/reduction, Mitsunobu's reaction, olefination/dihydroxylation, and epoxidation/ring-opening protocols. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.010