Convenient Synthesis and Purification of N-Trifluoroacetylated Neuraminic Acid Tetraol: A Key Precursor for the Synthesis of New Sialyl Donors Containing Labile O-Acyl Protecting Groups

被引：6

作者：

Podvalnyy, Nikita M. ^{[1
]}

Zinin, Alexander I. ^{[1
]}

Malysheva, Nelly N. ^{[1
]}

Kunetskiy, Roman A. ^{[1
]}

Kononov, Leonid O. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2014年 / 33卷 / 05期

关键词：

Sialic acid; Trifluoroacetamide; Crystal solvate; O-Trifluoroacetylation; GLYCOSYL DONOR; PHOSPHITE; GANGLIOSIDE;

D O I：

10.1080/07328303.2014.913058

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A convenient synthesis and separation of alpha- and beta-anomers of methyl (phenyl 3, 5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-nonulopyranosid) onate (6a and 6b) on a multigram scale was developed. Both alpha- and beta-isomers of 6 were obtained as crystals suitable for safe storage. The beta-isomer forms a crystalline solvate with methanol. Fully O-trichloroacetylated and O-trifluoroacetylated N-trifluoroacetyl thiosialosides were synthesized in an efficient manner from the beta-tetraol 6b.

引用

页码：213 / 224

页数：12

共 2 条

[1] Synthesis of 1-β-O-acyl glucuronides of diclofenac, mefenamic acid and (S)-naproxen by the chemo-selective enzymatic removal of protecting groups from the corresponding methyl acetyl derivatives
Baba, Akiko
Yoshioka, Tadao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (17) : 3303 - 3310
[2] New mild acid-labile protecting groups for the guanidino function of N-alpha-fluorenylmethoxycarbonyl-L-arginine in solid-phase peptide synthesis: 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl, 2-methoxy-10,11-dihydoro-5H-dibenzo[a,d]cyclopenten-5-yl and 5H-dibenzo[a,d]cyclohepten-5-yl groups
Noda, M
Kiffe, M
JOURNAL OF PEPTIDE RESEARCH, 1997, 50 (05): : 329 - 335

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