(1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol | 677745-86-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol
• 英文别名: (1R,2R,3S,4R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4-bis(methoxymethoxy)cyclohexane-1,2-diol
• CAS: 677745-86-7
• 化学式: C₂₇H₄₀O₇Si
• 分子量: 504.696
• InChiKey: CWMCOXCMCHWGJZ-VKQKEIENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol 在 4 A molecular sieve 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 Benzoic acid (1S,3R,5R,6R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-5,6-bis-methoxymethoxy-2-oxo-cyclohexyl ester
  参考文献：
  名称：

  Practical syntheses of enantiopure carbasugars: carba-β-altrose, carba-β-mannose, carba-β-idose, and carba-β-talose derivatives

  摘要：

  D and L forms of carba-beta-altrose 8, carba-beta-mannose 10a, carba-beta-idose 12, carba-beta-talose 14 derivatives were prepared from (+/-)-3-cyclohexene-1-carboxylic acid 1. Homochiral diol compounds D-5a and L-5a, which were prepared from 1 via enzyme resolution of (+/-)-4a, were efficiently transformed to carba-beta-altrose derivatives 8 by stereoselective introduction of hydroxyl groups. Oxidation (PCC)/reduction (NaBH4) of 3-OH and/or 4-OH of 8a efficiently gave 10a, 12, and 14 with good stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.042
• 作为产物：
  描述：

  在 四氧化锇 、 sodium methylate 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 生成 (1R,2R,3S,4R,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3,4-bis-methoxymethoxy-cyclohexane-1,2-diol
  参考文献：
  名称：

  Practical syntheses of enantiopure carbasugars: carba-β-altrose, carba-β-mannose, carba-β-idose, and carba-β-talose derivatives

  摘要：

  D and L forms of carba-beta-altrose 8, carba-beta-mannose 10a, carba-beta-idose 12, carba-beta-talose 14 derivatives were prepared from (+/-)-3-cyclohexene-1-carboxylic acid 1. Homochiral diol compounds D-5a and L-5a, which were prepared from 1 via enzyme resolution of (+/-)-4a, were efficiently transformed to carba-beta-altrose derivatives 8 by stereoselective introduction of hydroxyl groups. Oxidation (PCC)/reduction (NaBH4) of 3-OH and/or 4-OH of 8a efficiently gave 10a, 12, and 14 with good stereoselectivity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.042

文献信息

• Divergent syntheses of all 16 carbasugar stereoisomers via stereoconversion of carba-β-d-altropyranose derivatives
  作者：Seok-Ho Yu、Sung-Kee Chung

  DOI：10.1016/j.tetasy.2005.07.010

  日期：2005.8

  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.