Synthesis of 1-deoxy-4-thio-D-ribose starting from thiophene-2-carboxylic acid

被引：9

作者：

Altenbach, HJ

Brauer, DJ

Merhof, GF

机构：

[1] Bergische Univ.-Gesamthochsch. W., Fachbereich Chemie, D-42097 Wuppertal

来源：

TETRAHEDRON | 1997年 / 53卷 / 17期

关键词：

D O I：

10.1016/S0040-4020(97)00290-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The de novo synthesis of 1-deoxy-4-thio-D-ribose starting from thiophene-2-carboxylic acid is described, The key step is the cis-dihydroxylation of S-2-acetoxy-2, 5-dihydrothiophene, which is obtained by enzymatic alcoholysis. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：6019 / 6026

页数：8

相关论文

共 25 条

[1] Synthesis of 1-deoxy-4-thio-L-ribose starting from D-arabitol [J].

Altenbach, HJ ;

Merhof, GF .

TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3087-3090

[2] S-(-)-2-acetoxymethyl-2,5-dihydrothiophene via enzymatic resolution [J].

Altenbach, HJ ;

Merhof, GF ;

Brauer, DJ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (09) :2493-2496

[3]

ANISUZZAMAN AKM, 1978, J BANGLADESH ACAD SC, V2, P60

[4]

Bartlett P.A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[5] A NEW APPROACH TO 5-THIOSUGARS - 5-THIO-D-GLUCONHYDROXIMO-1,5-LACTONE, SYNTHESIS AND EVALUATION AS BETA-GLUCOSIDASE INHIBITOR [J].

ERMERT, P ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1993, 76 (07) :2687-2699

[6]

FATIADI AJ, 1987, SYNTHESIS-STUTTGART, P85

[7] 4'-THIONUCLEOSIDES VIA IN-SITU PYRANOSE-FURANOSE REARRANGEMENTS - A SHORT SYNTHESIS OF THE ANTIHERPES AGENT 2'-DEOXY-5-ETHYL-4'-THIOURIDINE VIA DIRECT COUPLING OF A SILYLATED PYRIMIDINE BASE WITH A 4-THIOPYRANOSE SUGAR [J].

JANDU, KS ;

SELWOOD, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5170-5173

[8]

JOULLIE MM, 1983, J ORG CHEM, V48, P3206

[9]

JOULLIE MM, 1981, SYNTHETIC COMMUN, V11, P881

[10] A MILD, OSMIUM TETRAOXIDE-CATALYZED METHOD FOR THE OXIDATION OF SULFIDES TO SULFONES [J].

KALDOR, SW ;

HAMMOND, M .

TETRAHEDRON LETTERS, 1991, 32 (38) :5043-5046