A practical synthesis of L-ribose

被引:29
作者
Akagi, M [1 ]
Omae, D [1 ]
Tamura, Y [1 ]
Ueda, T [1 ]
Kumashiro, T [1 ]
Urata, H [1 ]
机构
[1] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan
关键词
mirror image; L-ribose; L-RNA; L-nucleoside;
D O I
10.1248/cpb.50.866
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
L-Ribose was synthesized by a simple four-step method with overall yield of 76.3% from a protected L-arabinose derivative, which is a compatible intermediate for the synthesis of l: deoxyribose. The key step of this strategy is the Swern oxidation and subsequent stereo selective reduction accompanied by inversion of the 2-hydroxy group of protected L-arabinose.
引用
收藏
页码:866 / 868
页数:3
相关论文
共 27 条
[1]  
ABE Y, 1980, CHEM PHARM BULL, V28, P1324
[2]   SYNTHESIS OF L-RIBOFURANOSE + L-ADENOSINE [J].
ACTON, EM ;
RYAN, KJ ;
GOODMAN, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (23) :5352-&
[3]   PREPARATION AND CHARACTERIZATION OF OLIGONUCLEOTIDES OF D-2' AND L-2' DEOXYURIDINE [J].
ANDERSON, DJ ;
REISCHER, RJ ;
TAYLOR, AJ ;
WECHTER, WJ .
NUCLEOSIDES & NUCLEOTIDES, 1984, 3 (05) :499-512
[4]   MODELING, SYNTHESIS, AND HYBRIDIZATION PROPERTIES OF (L)-RIBONUCLEIC ACID [J].
ASHLEY, GW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (25) :9731-9736
[5]   NEW SYNTHESIS OF L-RIBOFURANOSE DERIVATIVES FROM L-ARABINOSE [J].
BATCH, A ;
CZERNECKI, S .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (06) :935-940
[6]   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
[7]   NEW SYNTHESIS OF L-RIBOFURANOSE DERIVATIVES FROM L-XYLOSE [J].
CHELAIN, E ;
FLOCH, O ;
CZERNECKI, S .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (08) :1251-1256
[8]   A practical synthesis of L-FMAU from L-arabinose [J].
Du, JF ;
Choi, Y ;
Lee, K ;
Chun, BK ;
Hong, JH ;
Chu, CK .
NUCLEOSIDES & NUCLEOTIDES, 1999, 18 (02) :187-195
[9]   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
[10]   TAR-RNA binding by HIV-1 Tat protein is selectively inhibited by its L-enantiomer [J].
Garbesi, A ;
Hamy, F ;
Maffini, M ;
Albrecht, G ;
Klimkait, T .
NUCLEIC ACIDS RESEARCH, 1998, 26 (12) :2886-2890