3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-altropyranose | 867258-56-8

• 英文名称: 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-altropyranose
• CAS: 867258-56-8
• 化学式: C₃₉H₄₈O₆Si
• 分子量: 640.892
• InChiKey: WYMSKUIRIZSRMI-OZQFTSORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-altropyranose 在 sodium tetrahydroborate 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-allopyranose
  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：

  2-O-benzoyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-5a-carba-α-D-altropyranose 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 3,4-di-O-benzyl-6-O-(tert-butyldiphenyl)silyl-1-O-methoxymethyl-5a-carba-α-D-altropyranose
  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