(1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene | 867258-59-1

• 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: (1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene
• CAS: 867258-59-1
• 化学式: C₃₇H₄₂O₃Si
• 分子量: 562.824
• InChiKey: BLFKWDWAVJEXGA-RFFQGONESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene 在 盐酸 、 N-碘代丁二酰亚胺 、 溶剂黄146 、 lithium bromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 (1S,2R,3S,4R,5R)-3,4-Bis-benzyloxy-2-bromo-5-(tert-butyl-diphenyl-silanyloxymethyl)-cyclohexanol
  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-1,2-di-O-(methoxymethyl)-5a-carba-β-D-mannopyranose 在 咪唑 、 三甲基溴硅烷 、 4 A molecular sieve 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.42h， 生成 (1R,2R,3R)-1,2-di-benzyloxy-3-(tert-butyldiphenyl-silanyloxymethyl)-cyclohex-5-ene
  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