methyl 6-((4R,5R)-5-((acetylthio)methyl)-1,3-dibenzyl-2-oxoimidazolidin-4-yl)-6-oxohexanoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 6-((4R,5R)-5-((acetylthio)methyl)-1,3-dibenzyl-2-oxoimidazolidin-4-yl)-6-oxohexanoate
• 英文别名: methyl 6-[(4R,5R)-5-(acetylsulfanylmethyl)-1,3-dibenzyl-2-oxoimidazolidin-4-yl]-6-oxohexanoate
• 化学式: C₂₇H₃₂N₂O₅S
• 分子量: 496.627
• InChiKey: QDGREPUVDXHPON-JYFHCDHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-((4R,5R)-5-((acetylthio)methyl)-1,3-dibenzyl-2-oxoimidazolidin-4-yl)-6-oxohexanoate 在 lipase from Candida rugosa 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 aq. phosphate buffer 、 甲苯 为溶剂， 反应 9.0h， 生成 (3aS,4Z,6aR)-5-{hexahydro-1,3-dibenzyl-2-oxo-4H-thieno[3,4-d]imidazol-4-ylidene}pentanoic acid methyl ester
  参考文献：
  名称：

  A novel and enantioselective synthesis of d-(+)-biotin via a Sharpless asymmetric dihydroxylation strategy

  摘要：

  A novel and enantioselective synthesis of D-(+)-biotin has been accomplished starting from commercially available cyclohexanone. The key steps in the sequence are the Sharpless asymmetric dihydroxylation of a (E)-ethyl 3-(2-chlorocyclohex-1-en-1-yl)acrylate derivative to establish the stereocenters of D-(+)-biotin, the carboxyalkyl side chain is introduced by unmasking the cyclohexene by ozonolysis and enzymatic hydrolysis of a thioacetate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.002
• 作为产物：
  描述：

  2-氯-1-甲酰基-1-环己烯 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四氧化锇 、 氯化亚砜 、 sodium azide 、 甲基磺酰胺 、 camphor-10-sulfonic acid 、 水 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 臭氧 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 179.67h， 生成 methyl 6-((4R,5R)-5-((acetylthio)methyl)-1,3-dibenzyl-2-oxoimidazolidin-4-yl)-6-oxohexanoate
  参考文献：
  名称：

  A novel and enantioselective synthesis of d-(+)-biotin via a Sharpless asymmetric dihydroxylation strategy

  摘要：

  A novel and enantioselective synthesis of D-(+)-biotin has been accomplished starting from commercially available cyclohexanone. The key steps in the sequence are the Sharpless asymmetric dihydroxylation of a (E)-ethyl 3-(2-chlorocyclohex-1-en-1-yl)acrylate derivative to establish the stereocenters of D-(+)-biotin, the carboxyalkyl side chain is introduced by unmasking the cyclohexene by ozonolysis and enzymatic hydrolysis of a thioacetate. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.10.002

文献信息

• A novel and enantioselective synthesis of d-(+)-biotin via a Sharpless asymmetric dihydroxylation strategy
  作者：Subhash P. Chavan、Pradeep B. Lasonkar、Prakash N. Chavan

  DOI：10.1016/j.tetasy.2013.10.002

  日期：2013.12

  A novel and enantioselective synthesis of D-(+)-biotin has been accomplished starting from commercially available cyclohexanone. The key steps in the sequence are the Sharpless asymmetric dihydroxylation of a (E)-ethyl 3-(2-chlorocyclohex-1-en-1-yl)acrylate derivative to establish the stereocenters of D-(+)-biotin, the carboxyalkyl side chain is introduced by unmasking the cyclohexene by ozonolysis and enzymatic hydrolysis of a thioacetate. (C) 2013 Elsevier Ltd. All rights reserved.