Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323

被引：55

作者：

Pierce, ME ^{[1
]}

Harris, GD ^{[1
]}

Islam, Q ^{[1
]}

Radesca, LA ^{[1
]}

Storace, L ^{[1
]}

Waltermire, RE ^{[1
]}

Wat, E ^{[1
]}

Jadhav, PK ^{[1
]}

Emmett, GC ^{[1
]}

机构：

[1] DUPONT MERCK PHARMACEUT CO,EXPTL STN,DEPT CHEM & PHYS SCI,WILMINGTON,DE 19880

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期

关键词：

D O I：

10.1021/jo951847u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C-2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led to intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed to prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.

引用

页码：444 / 450

页数：7

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