1,6-diphenyl-5(S)-tert-butoxycarbonylamino-3(S)-hydroxy-2(S)-phenylmethoxy-carbonylaminohexane | 1448312-65-9

• 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: 1,6-diphenyl-5(S)-tert-butoxycarbonylamino-3(S)-hydroxy-2(S)-phenylmethoxy-carbonylaminohexane
• 英文别名: benzyl tert-butyl ((2S,3S,5S)-3-hydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate；tert-butyl N-[(2S,4S,5S)-4-hydroxy-1,6-diphenyl-5-(phenylmethoxycarbonylamino)hexan-2-yl]carbamate
• CAS: 1448312-65-9
• 化学式: C₃₁H₃₈N₂O₅
• 分子量: 518.653
• InChiKey: WMJHBHRBPBVGGW-KCHLEUMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-diphenyl-5(S)-tert-butoxycarbonylamino-3(S)-hydroxy-2(S)-phenylmethoxy-carbonylaminohexane 在 盐酸 、 水 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides

  摘要：

  The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.033
• 作为产物：
  描述：

  氯甲酸苄酯 、 [(1S,3S,4S)-4-氨基-3-羟基-5-苯基-1-(苯甲基)戊基]-氨基甲酸叔丁酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到1,6-diphenyl-5(S)-tert-butoxycarbonylamino-3(S)-hydroxy-2(S)-phenylmethoxy-carbonylaminohexane
  参考文献：
  名称：

  [EN] METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS
  [FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION D'AGENTS PHARMACEUTIQUES

  摘要：

  用于制备式I化合物及其盐的方法和中间体。

  公开号：

  WO2013116715A1

文献信息

• METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS
  申请人：Gilead Sciences, Inc.

  公开号：US20140364602A1

  公开（公告）日：2014-12-11

  Methods and intermediates useful for preparing a compound of formula I: and salts thereof.

  用于制备化合物I的方法和中间体，以及其盐。
• US9346796B2
  申请人：——

  公开号：US9346796B2

  公开（公告）日：2016-05-24
• [EN] METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS<br/>[FR] PROCÉDÉS ET INTERMÉDIAIRES POUR LA PRÉPARATION D'AGENTS PHARMACEUTIQUES
  申请人：GILEAD SCIENCES INC

  公开号：WO2013116715A1

  公开（公告）日：2013-08-08

  Methods and intermediates useful for preparing a compound of formula I and salts thereof.

  用于制备式I化合物及其盐的方法和中间体。
• Synthesis of hydantoins and dihydrouracils via thermally-promoted cyclization of ureidoacetamides
  作者：Michael C. Hillier、Hai-Hua Gong、Dean S. Clyne、Martin J. Babcock

  DOI：10.1016/j.tet.2014.10.033

  日期：2014.12

  The synthesis of hydantoins and dihydrouracils from ureidoacetamides has been carried out at high temperature in glycol solvents. A series of substrates were prepared and examined to determine the effect of substrate structure, N-acyl substitution (X), and solvent on the course of the reaction. A dramatic effect was observed when using ureidoacetamides (e.g., X=N-methyl-N-phenyl), which led to higher yields, faster reaction times, and lower racemization of chiral substrates. The rate of racemization of a chiral hydantoin in the presence of dibenzylamine and N-methyl aniline has also been determined. The thermal cyclization methodology has been applied to the preparation of a complex hydantoin. (C) 2014 Elsevier Ltd. All rights reserved.