(2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone | 867258-53-5

• 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: (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone
• CAS: 867258-53-5
• 化学式: C₃₉H₄₆O₆Si
• 分子量: 638.876
• InChiKey: JVCCPJYQRPURPQ-PCSLLBDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 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：
  0.36
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-cyclohexanone 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到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 4 A molecular sieve 、 sodium methylate 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 40.0h， 生成 (2R,3S,4S,6R)-2,3-benzyloxy-4-(tert-butyldiphenylsilanyloxymethyl)-6-methoxymethyloxy-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