(4S,5S,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one) | 143838-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5S,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one)
• 英文别名: (4S,5S)-4-benzyl-5-[(4S,5S)-4-benzyl-2-oxo-1,3-oxazolidin-5-yl]-1,3-oxazolidin-2-one
• CAS: 143838-08-8
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: PNQRSXPLZLDQDT-XSLAGTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5S)-2,5-bis<<(tert-butyloxy)carbonyl>amino>-3,4-dihydroxy-1,6-diphenylhexane 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 生成 (4S,5S,4'S,5'S)-5,5'-bis(4-benzyloxazolidin-2-one)
  参考文献：
  名称：

  Stereocontrolled synthesis of C2-symmetric and pseudo-C2-symmetric diamino alcohols and diols for use in HIV protease inhibitors

  摘要：

  The stereocontrolled syntheses of dibenzyldiamino alcohol 1 and dibenzyldiamino diols 2-4, core units of potent C2-symmetric and pseudo-C2-symmetric inhibitors of HIV protease, are described, starting from phenylalanine. Stereoselective epoxidation of trans olefin 7, produced by S(N)2' displacement of an allylic mesylate, followed by regiospecific epoxide opening with lithium azide provided the azido alcohol 8 as the major product. Azide reduction and deprotection led to diamine 1. Protected diamino diols 15-17 were prepared expeditiously by intermolecular titanium- or vanadium-mediated pinacol coupling of protected phenylalaninal. Methods for the stereospecific interconversion of the major (3R,4R,5R,6S) isomer to the desired (3S,4R,5S,6S) isomer via intramolecular hydroxyl inversion are described.

  DOI：

  10.1021/jo00047a023

文献信息

• Synthesis of C2-symmetric dibenzyldiamino diols by double stereoselective grignard addition to (S,S)-tartraldehyde dinitrone
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1016/s0040-4039(98)00330-x

  日期：1998.4

  A new asymmetric two-dimensional synthesis of 1,4-diamino 2,3-diols is illustrated by double addition of benzylmagnesium chloride to the bis-nitrone derived from (R,R)-tartraldehyde and reduction of the resulting dihydroxylamines.

  通过将苄基氯化镁双加到衍生自（R，R）-酒石醛的双硝基并还原生成的二羟胺来说明1,4-二氨基2,3-二醇的新的不对称二维合成。
• Intermediates for preparing retroviral protease inhibiting compounds
  申请人：Abbott Laboratories

  公开号：EP0997459A1

  公开（公告）日：2000-05-03

  An intermediate of the formula: and an intermediate of the formula: or an acid addition salt thereof.

  公式的中间体： 和 式的中间体 或其酸加成盐。
• Grignard Addition to Aldonitrones. Stereochemical Aspects and Application to the Synthesis of C₂-Symmetric Diamino Alcohols and Diamino Diols
  作者：Alessandro Dondoni、Daniela Perrone、Marilisa Rinaldi

  DOI：10.1021/jo980980u

  日期：1998.12.1

  A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4-diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from beta-amino-alpha-hydroxy aldehydes followed by reduction of the resulting N-benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3-diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV-1 protease inhibitors.
• Retroviral protease inhibiting compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0486948B1

  公开（公告）日：2000-10-04
• US5354866A
  申请人：——

  公开号：US5354866A

  公开（公告）日：1994-10-11