Novel synthesis of L-ribose from D-mannono-1,4-lactone

被引：41

作者：

Takahashi, H ^{[1
]}

Iwai, Y ^{[1
]}

Hitomi, Y ^{[1
]}

Ikegami, S ^{[1
]}

机构：

[1] Teikyo Univ, Fac Pharmaceut Sci, Sagamiko, Kanagawa 1990195, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 14期

关键词：

D O I：

10.1021/ol026141i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] D-Mannono-1,4-lactone was efficiently converted into L-ribose in eight steps. A key step of this synthesis is the cyclization of a gamma-hydroxyalkoxamate under Mitsunobu conditions. It is noteworthy that the O-alkylation product was obtained in 94% yield and that none of the N-alkylation product was detected in this cyclization.

引用

页码：2401 / 2403

页数：3

共 26 条

[1]

Anderson Karen S., 2001, Antiviral Chemistry and Chemotherapy, V12, P13

[2] MODELING, SYNTHESIS, AND HYBRIDIZATION PROPERTIES OF (L)-RIBONUCLEIC ACID [J].

ASHLEY, GW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :9731-9736

[3]

BASHA A, 1977, TETRAHEDRON LETT, P4171

[4] STEREOSELECTIVE CHIRAL SYNTHESIS OF N-ARYL-ALPHA-AMINO-BETA-LACTAMS FROM BETA-HYDROXY-ALPHA-AMINO ACIDS [J].

BOSE, AK ;

SAHU, DP ;

MANHAS, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1229-1230

[5]

CHEN SH, 2001, FRONT BIOTECHNOL PHA, V2, P307

[6] ANTISENSE L/D-OLIGODEOXYNUCLEOTIDE CHIMERAS - NUCLEASE STABILITY, BASE-PAIRING PROPERTIES, AND ACTIVITY AT DIRECTING RIBONUCLEASE-H [J].

DAMHA, MJ ;

GIANNARIS, PA ;

MARFEY, P .

BIOCHEMISTRY, 1994, 33 (25) :7877-7885

[7] FACILE SYNTHESES AND REARRANGEMENTS OF PEPTIDE DERIVED BETA-LACTAMS [J].

FAROUZ, F ;

MILLER, MJ .

TETRAHEDRON LETTERS, 1991, 32 (28) :3305-3308

[8] ENANTIO-DNA RECOGNIZES COMPLEMENTARY RNA BUT NOT COMPLEMENTARY-DNA [J].

FUJIMORI, S ;

SHUDO, K ;

HASHIMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7436-7438

[9] FORMATION OF OXAZOLINES AND THIAZOLINES IN PEPTIDES BY THE MITSUNOBU REACTION [J].

GALEOTTI, N ;

MONTAGNE, C ;

PONCET, J ;

JOUIN, P .

TETRAHEDRON LETTERS, 1992, 33 (20) :2807-2810

[10] L-nucleosides as chemotherapeutic agents [J].

Gumina, G ;

Song, GY ;

Chu, CK .

FEMS MICROBIOLOGY LETTERS, 2001, 202 (01) :9-15

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