A new efficient and practical synthesis of 2-deoxy-L-ribose

被引：35

作者：

Cho, BH ^{[1
]}

Kim, JH ^{[1
]}

Jeon, HB ^{[1
]}

Kim, KS ^{[1
]}

机构：

[1] Yonsei Univ, Ctr Bioact Mol Hybrids, Dept Chem, Seoul 120749, South Korea

来源：

TETRAHEDRON | 2005年 / 61卷 / 18期

关键词：

L-enantiomer; largc-scale synthesis; epoxide-ring opening; nitrile;

D O I：

10.1016/j.tet.2005.03.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical route for large-scale synthesis of 2-deoxy-L-ribose starting from L-ascorbic acid was developed in eight steps without chromatographic purification for all intermediates. Additionally, (2S,3R)-3,4-epoxy-1,2-O-isopropylidenebutane-1,2-diol, a versatile intermediate in carbohydrate synthesis, was also prepared readily in excellent yield as a key intermediate. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4341 / 4346

页数：6

共 51 条

[1] THE CHEMISTRY OF L-ASCORBIC AND D-ISOASCORBIC ACIDS .1. THE PREPARATION OF CHIRAL BUTANETRIOLS AND BUTANETETROLS [J].

ABUSHANAB, E ;

VEMISHETTI, P ;

LEIBY, RW ;

SINGH, HK ;

MIKKILINENI, AB ;

WU, DCJ ;

SAIBABA, R ;

PANZICA, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2598-2602

[2]

AGROFOGLIO LA, 1998, CHEM L NUCLEOSIDES, P285

[3] SYNTHESIS AND PHYSICOCHEMICAL PROPERTIES OF OLIGONUCLEOTIDES BUILT WITH EITHER ALPHA-L OR BETA-L NUCLEOTIDES UNITS AND COVALENTLY LINKED TO AN ACRIDINE DERIVATIVE [J].

ASSELINE, U ;

HAU, JF ;

CZERNECKI, S ;

LEDIGUARHER, T ;

PERLAT, MC ;

VALERY, JM ;

THUONG, NT .

NUCLEIC ACIDS RESEARCH, 1991, 19 (15) :4067-4074

[4] SYNTHESIS OF ENANTIOMERICALLY PURE (2'R,5'S)-(-)-1-[2-(HYDROXYMETHYL)OXATHIOLAN-5-YL]CYTOSINE AS A POTENT ANTIVIRAL AGENT AGAINST HEPATITIS-B VIRUS (HBV) AND HUMAN-IMMUNODEFICIENCY-VIRUS (HIV) [J].

BEACH, JW ;

JEONG, LS ;

ALVES, AJ ;

POHL, D ;

KIM, HO ;

CHANG, CN ;

DOONG, SL ;

SCHINAZI, RF ;

CHENG, YC ;

CHU, CK .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2217-2219

[5] THE SYNTHESIS OF MODIFIED OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH AND THEIR APPLICATIONS [J].

BEAUCAGE, SL ;

IYER, RP .

TETRAHEDRON, 1993, 49 (28) :6123-6194

[6] Anti-human immunodeficiency and anti-hepatitis B virus activities of beta-L-2',3'-dideoxy purine nucleosides [J].

Bolon, PJ ;

Wang, PY ;

Chu, CK ;

Gosselin, G ;

Boudou, V ;

Pierra, C ;

Mathe, C ;

Imbach, JL ;

Faraj, A ;

Alaoui, MA ;

Sommadossi, JP ;

Pai, SB ;

Zhu, YL ;

Lin, JS ;

Cheng, YC ;

Schinazi, RF .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (14) :1657-1662

[7]

CHANG CN, 1992, J BIOL CHEM, V267, P22414

[8]

CHANG CN, 1992, J BIOL CHEM, V267, P13938

[9] Efficient synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) from L-arabinose [J].

Chong, YH ;

Chu, CK .

CARBOHYDRATE RESEARCH, 2002, 337 (05) :397-402

[10] USE OF 2'-FLUORO-5-METHYL-BETA-L-ARABINOFURANOSYLURACIL AS A NOVEL ANTIVIRAL AGENT FOR HEPATITIS-B VIRUS AND EPSTEIN-BARR-VIRUS [J].

CHU, CK ;

MA, TW ;

SHANHMUGANATHAN, K ;

WANG, CG ;

XIANG, YJ ;

PAI, SB ;

YAO, GQ ;

SOMMADOSSI, JP ;

CHENG, YC .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (04) :979-981

← 1 2 3 4 5 6 →