(2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane | 136985-06-3

• 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: (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane
• 英文别名: [(2S,3R,4R)-4-[bis(ethylsulfanyl)methyl]-2-[(2S,3R)-3-[(2-methylpropan-2-yl)oxy]-2-(phenylmethoxycarbonylamino)butanoyl]oxyoctan-3-yl] 3-methylbutanoate
• CAS: 136985-06-3
• 化学式: C₃₄H₅₇NO₇S₂
• 分子量: 655.961
• InChiKey: VNHKFUIJFRNYIY-WUCHJKDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  44.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane 在 无水碳酸镉 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 5.33h， 生成 (2S,3R)-2-Benzyloxycarbonylamino-3-tert-butoxy-butyric acid (1S,2R,3R)-3-formyl-1-methyl-2-(3-methyl-butyryloxy)-heptyl ester
  参考文献：
  名称：

  Organoaluminium induced ring-opening of epoxypyranosides. V. Formal total synthesis of antimycin A3 and synthesis of (+)-blastmycinone.

  摘要：

  Epoxide ring-opening of the benzyl 2,3-anhydro-alpha-L-ribopyranoside 6 with lithium butynyl(trimethyl)-aluminate followed by functional group interconventions gave the dihydroxy thioacetal 11, which was regio-selectively acylated with an L-threonine derivative. Acylation of the remaining hydroxyl group with isovaleryl chloride followed by thioacetal hydrolysis and oxidation of the liberated aldehyde gave 14, an intermediate in Kinoshita's antimycin A3 synthesis. The stereostructure of 11 was confirmed by converting it into (-)-blastmycino-lactol (18) which was acylated with isovaleryl chloride to give (+)-blastmycinone (19).

  DOI：

  10.1016/s0040-4020(01)86575-3
• 作为产物：
  描述：

  benzyl 2,3-anhydro-α-L-ribopyranoside 在 Wilkinson's catalyst 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 氢气 、 三甲基铝 、 N,N'-二环己基碳二亚胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -70.0~60.0 ℃ 、101.33 kPa 条件下， 反应 53.25h， 生成 (2R, 3R, 4S) 4-(N-benzyloxycarbonyl-O-tert-butyl-L-threonyloxy)-2-butyl-1,1-bis(ethylthio)-3-isovaleryloxy-pentane
  参考文献：
  名称：

  Organoaluminium induced ring-opening of epoxypyranosides. V. Formal total synthesis of antimycin A3 and synthesis of (+)-blastmycinone.

  摘要：

  Epoxide ring-opening of the benzyl 2,3-anhydro-alpha-L-ribopyranoside 6 with lithium butynyl(trimethyl)-aluminate followed by functional group interconventions gave the dihydroxy thioacetal 11, which was regio-selectively acylated with an L-threonine derivative. Acylation of the remaining hydroxyl group with isovaleryl chloride followed by thioacetal hydrolysis and oxidation of the liberated aldehyde gave 14, an intermediate in Kinoshita's antimycin A3 synthesis. The stereostructure of 11 was confirmed by converting it into (-)-blastmycino-lactol (18) which was acylated with isovaleryl chloride to give (+)-blastmycinone (19).

  DOI：

  10.1016/s0040-4020(01)86575-3

文献信息

• INGHARDT, TORD;FREJD, TORBJORN, TETRAHEDRON, 47,(1991) N2, C. 6483-6492
  作者：INGHARDT, TORD、FREJD, TORBJORN

  DOI：——

  日期：——