A SIMPLE STRATEGY FOR THE SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERE FROM D-GLUCOSE

被引：9

作者：

CHAKRABORTY, TK

HUSSAIN, KA

THIPPESWAMY, D

机构：

[1] Indian Institute of Chemical Technology, Hyderabad

来源：

TETRAHEDRON | 1995年 / 51卷 / 13期

关键词：

D O I：

10.1016/0040-4020(95)00109-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach is outlined here for the synthesis of hydroxyethylene dipeptide isostere (1) starting from D-glucose which can be employed to introduce any group at P-1 or P-1, positions of such isosteres. A highly stereoselective synthesis of (2R,4S,5S)-N-Boc-O-benzyl-5-amino-4-hydroxy-2-methyl-6-phenylhexanoic acid methyl ester (2) is accomplished based on this strategy.

引用

页码：3873 / 3880

页数：8

共 26 条

[1] AN INHIBITOR OF THE PROTEASE BLOCKS MATURATION OF HUMAN AND SIMIAN IMMUNODEFICIENCY VIRUSES AND SPREAD OF INFECTION
ASHORN, P
MCQUADE, TJ
THAISRIVONGS, S
TOMASSELLI, AG
TARPLEY, WG
MOSS, B
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (19) : 7472 - 7476
[2] THE RING-OPENING OF AZIRIDINE-2-CARBOXYLATE ESTERS WITH ORGANOMETALLIC REAGENTS
BALDWIN, JE
ADLINGTON, RM
ONEIL, IA
SCHOFIELD, C
SPIVEY, AC
SWEENEY, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) : 1852 - 1854
[3] BENDITT J, 1993, SCIENCE, V260, P1253
[4] CARR TJ, 1992, BIOCHEMISTRY-US, V343, P6646
[5] STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR
CHAKRABORTY, TK
GANGAKHEDKAR, KK
[J]. TETRAHEDRON LETTERS, 1991, 32 (16) : 1897 - 1898
[6] SYNTHESIS OF C2-SYMMETRICAL AND PSEUDOSYMMETRIC HIV-1 PROTEASE INHIBITORS FROM D-MANNITOL AND D-ARABITOL
CHENERA, B
BOEHM, JC
DREYER, GB
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (04) : 219 - 222
[7] INHIBITION OF HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE INVITRO - RATIONAL DESIGN OF SUBSTRATE-ANALOG INHIBITORS
DREYER, GB
METCALF, BW
TOMASZEK, TA
CARR, TJ
CHANDLER, AC
HYLAND, L
FAKHOURY, SA
MAGAARD, VW
MOORE, ML
STRICKLER, JE
DEBOUCK, C
MEEK, TD
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (24) : 9752 - 9756
[8] HYDROXYETHYLENE ISOSTERE INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS-1 PROTEASE - STRUCTURE ACTIVITY ANALYSIS USING ENZYME-KINETICS, X-RAY CRYSTALLOGRAPHY, AND INFECTED T-CELL ASSAYS
DREYER, GB
LAMBERT, DM
MEEK, TD
CARR, TJ
TOMASZEK, TA
FERNANDEZ, AV
BARTUS, H
CACCIAVILLANI, E
HASSELL, AM
MINNICH, M
PETTEWAY, SR
METCALF, BW
LEWIS, M
[J]. BIOCHEMISTRY, 1992, 31 (29) : 6646 - 6659
[9] NUCLEOPHILIC OPENING OF CHIRAL BIS(AZIRIDINES) - A ROUTE TO ENANTIOMERICALLY PURE ALPHA-AMINO ALDEHYDES OR ACIDS AND POLYSUBSTITUTED PIPERIDINES
DUREAULT, A
TRANCHEPAIN, I
DEPEZAY, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) : 5324 - 5330
[10] DUTTA AS, 1993, SMALL PEPTIDES CHEM, P482

← 1 2 3 →