CRCL2 MEDIATED ALLYLATION OF N-PROTECTED ALPHA-AMINO ALDEHYDES - A VERSATILE SYNTHESIS OF POLYPEPTIDES CONTAINING AN HYDROXYETHYLENE ISOSTERE

被引：38

作者：

CIAPETTI, P ^{[1
]}

TADDEI, M ^{[1
]}

ULIVI, P ^{[1
]}

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN UGO SCHIFF,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)76862-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Differently substituted allylic bromides react with N-protected amino aldehydes to give intermediate products for the synthesis of hydroxyethylene dipeptide isosteres. The low stereoselectivity of this reaction can be improved using aldehydes protected with hindered groups. This reaction can be efficiently applied to oligopetide aldehydes. We describe a protocol, for the preparation of peptides containing an hydroxyethylene isostere, which allows a rapid variations of the aminoacid sequence

引用

页码：3183 / 3186

页数：4

共 33 条

[31] SYNTHESIS AND MASS-SPECTROMETRIC STUDY OF LYSINE-CONTAINING PEPTIDES .2. EFFECT OF VARIOUS N-TERMINAL SUBSTITUENTS IN ALPHA-AMINO GROUP AND EPSILON-AMINO GROUP OF LYSINE ON MASS-SPECTROMETRIC BEHAVIOR OF LYSINE-CONTAINING PEPTIDES
ROSTOVTSEVA, LI
KHOKHLOV, AS
ZHURNAL OBSHCHEI KHIMII, 1975, 45 (10): : 2323 - 2331
[32] STUDIES ON BETA-LACTAM SYNTHESIS .5. VERSATILE SYNTHESIS OF N-PROTECTED ALKYL 2-(TRANS-4-ALKYLTHIO-3-AMINO-2-OXO-1-AZETIDINYL)ACRYLATES (TRANS-7-AMINO-1,2-SECOCEPH-3-EM-4-CARBOXYLATES) BEARING MODIFIED SIDE-CHAINS
HOPPE, D
KLOFT, M
LIEBIGS ANNALEN DER CHEMIE, 1980, (10): : 1512 - 1526
[33] ISOTHIOCYANATE-MEDIATED CONDENSATION OF N-ACYL-ALPHA-AMINO ACIDS WITH AROMATIC-ALDEHYDES - ONE-POT SYNTHESIS OF 1,2-DISUBSTITUTED "4-ARYLMETHYLENE-2-IMIDAZOLIN-5-ONES
ASHARE, R
MUKERJEE, AK
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (07): : 762 - 764

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