1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose | 867258-74-0

• 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: 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose
• 英文别名: (1R,2S,3S,4R,6S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,3-bis(phenylmethoxy)-6-prop-2-enoxycyclohexan-1-ol
• CAS: 867258-74-0
• 化学式: C₄₀H₄₈O₅Si
• 分子量: 636.904
• InChiKey: SCXKFKUBXNNKNY-QQYMBSMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-idopyranose 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以99.8%的产率得到(2R,3S,4R,6R)-6-allyloxy-4-(tert-butyl-diphenylsilanyloxymethyl)-2,3-di-benzyloxy-cyclohexanone
  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：

  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-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.67h， 生成 1-O-allyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-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