3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose | 867258-70-6

• 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: 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose
• 英文别名: (1R,2R,3S,4S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-bis(phenylmethoxy)cyclohexane-1,2-diol
• CAS: 867258-70-6
• 化学式: C₃₇H₄₄O₅Si
• 分子量: 596.839
• InChiKey: GBSRCUVYMLBPEE-FEIGQPKUSA-N

物化性质

• 沸点：
  654.1±55.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose 在 原乙酸三甲酯 、 三氟甲磺酸 、 4 A molecular sieve 、 4-甲基苯磺酸吡啶 、 L-Selectride 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-gulopyranose
  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：

  在 三甲基溴硅烷 、 4 A molecular sieve 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-β-D-idopyranose
  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