(1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid | 676144-83-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid
• 英文别名: (1R,2S,3S,4S,5S)-2,5-bis[[tert-butyl(dimethyl)silyl]oxy]-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-triethylsilyloxycyclohexane-1-carboxylic acid
• CAS: 676144-83-5
• 化学式: C₃₀H₆₃NO₇Si₃
• 分子量: 634.089
• InChiKey: VTFGPTCWTHVIEN-RYWAYVEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.16
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到(1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216
• 作为产物：
  描述：

  5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone 在 nickel dichloride 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium tetrahydroborate 、 草酰氯 、 氨 、 sodium 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 65.17h， 生成 (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 6.¹ Diastereoselective Synthesis of 2-Deoxy-2-amino-5a-carba-β-l-mannopyranuronic Acid and 2-Deoxy-2-amino-5a-carba-β-l-mannopyranose

  摘要：

  Efficient, total syntheses of novel 2-deoxy-2-amino-5a-carba-beta-L-mannopyranuronic acid (1) and 2-deoxy-2-amino-5a-carba-beta-L-mannopyranose (2), a positional stereoisomer of validamine, have been achieved in 28% and 24% overall yields and in 12 steps and 13 steps, respectively, from 2-[(tert-butyldimethylsilyl)oxy]furan (3) and (2S)-2,3-O-isopropylideneglyceraldehyde N-benzyl imine (4) via two highly diastereoselective Mukaiyama aldol-related chemical maneuvers. The strategy, which furnishes the targeted carbasugars in enantiopure forms, allows for complete control of the configuration at all five contiguous stereocenters of the targets by utilizing the sole element of chirality present in the aldimine progenitor 4.

  DOI：

  10.1021/jo0357216