(3S,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol | 136904-91-1

• 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: (3S,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol
• 英文别名: (3S,4R,5R,6S,7S)-1,8-Bis[(tert-butyldimethylsilyl)oxy]-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol；(1R,2R,3S)-5-[tert-butyl(dimethyl)silyl]oxy-1-[(4S,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(dibenzylamino)-1-(methoxymethoxy)pentan-3-ol
• CAS: 136904-91-1；136983-67-0
• 化学式: C₃₉H₆₇NO₇Si₂
• 分子量: 718.134
• InChiKey: XHVAJPUUKPNXNB-JFKVGHNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  78.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3S,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到(3S,4R,5R,6S,7S)-4-(Dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octane-1,3,8-triol
  参考文献：
  名称：

  Total syntheses of (+)-castanospermine and (+)-1-epicastanospermine and their 1-O-acyl derivatives from a common chiral building block

  摘要：

  Stereoselective total syntheses of (+)-castanospermine (1) and (+)-1-epicastanospermine (2) and their 1-O-acyl derivatives 3-5 have been achieved via a noncarbohydrate-based approach utilizing allylic alcohol 9 as a common chiral building block. Epoxide 10, prepared from 9, underwent regioand stereoselective ring opening with Et2AlN(CH2Ph)2 to give amino alcohol 11, which was converted to aldehyde 15 in four steps. The aldol reaction of 15 with lithio ethyl acetate was predominantly anti selective and generated alpha-hydroxy ester 16 by a nonchelate Felkin-Anh pathway. Compound 16 was transformed into (+)-1-epicastanospermine (2) and its 1-O-acetyl and 1-O-butyryl derivatives (4 and 5) via the lactam intermediate 21. Alternatively, alpha-hydroxy ester 16 was converted to (+)-castanospermine (1) and its 1-O-acetyl derivative (3); these syntheses were achieved via reaction sequences involving the inversion of the C-3 configuration by the Mitsunobu process and 2-fold tandem cyclizations to form the indolizidine skeleton. The results of preliminary biological testing of compounds 2-5 for anti-HIV-1 activity in whole cells are presented.

  DOI：

  10.1021/jo00053a015
• 作为产物：
  描述：

  (3R,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 苯 为溶剂， 生成 (3S,4R,5R,6S,7S)-1,8-Bis<(tert-butyldimethylsilyl)oxy>-4-(dibenzylamino)-6,7-(isopropylidenedioxy)-5-(methoxymethoxy)octan-3-ol
  参考文献：
  名称：

  A total synthesis of (+)-Castanospermine

  摘要：

  A stereoselective total synthesis of (+)-castanospermine has been achieved via a non-carbohydrate approach utilizing a chiral allylic alcohol as a versatile building block.

  DOI：

  10.1016/s0040-4039(00)79888-1