Facile preparation of α-acyloxyacetaldehyde, a versatile intermediate in the synthesis of antiviral nucleosides

被引:13
作者
Du, JF [1 ]
Watanabe, KA [1 ]
机构
[1] Pharmasset Inc, Tucker, GA 30084 USA
关键词
nucleosides; synthesis; HIV-1; HBV;
D O I
10.1081/SCC-120037904
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This report describes a novel and simple method for the preparation of a versatile intermediate, alpha-acyloxyacetaldehyde and its acetals, and its application to the synthesis of 4-acetoxy-2-acyloxymethyl-1,3-oxathiolane, an important intermediate in the synthesis of biologically active nucleosides.
引用
收藏
页码:1925 / 1930
页数:6
相关论文
共 28 条
[1]   IODIDE CATALYSIS OF OXIDATIONS WITH DIMETHYL-SULFOXIDE - CONVENIENT 2-STEP SYNTHESIS OF ALPHA-DIKETONES FROM ALPHA-METHYLENE KETONES [J].
BAUER, DP ;
MACOMBER, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (13) :1990-1992
[2]  
BELLEAU B, 1989, 5 INT C AIDS MONTR C
[3]  
Belleau B, 1991, New 2-hydroxymethyl-5-substituted-13-oxathiolane derivativesuUseful as anti-retroviral agents for treating HIV infections, Patent No. [US5047407, 5047407]
[4]   INSITU COMPLEXATION DIRECTS THE STEREOCHEMISTRY OF N-GLYCOSYLATION IN THE SYNTHESIS OF OXATHIOLANYL AND DIOXOLANYL NUCLEOSIDE ANALOGS [J].
CHOI, WB ;
WILSON, LJ ;
YEOLA, S ;
LIOTTA, DC ;
SCHINAZI, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) :9377-9379
[5]  
CHOI WB, 1993, Patent No. 5210085
[6]   A cyclization approach toward five-membered heteroaromatic o-quinodimethanes via fused-3-sulfolenes [J].
Chou, TS ;
Tsai, CY ;
Lee, SJ .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1997, 44 (03) :299-307
[7]   ASYMMETRIC-SYNTHESIS OF ENANTIOMERICALLY PURE (-)-(1'R,4'R)-DIOXOLANE-THYMINE AND ITS ANTI-HIV ACTIVITY [J].
CHU, CK ;
AHN, SK ;
KIM, HO ;
BEACH, JW ;
ALVES, AJ ;
JEONG, LS ;
ISLAM, Q ;
VANROEY, P ;
SCHINAZI, RF .
TETRAHEDRON LETTERS, 1991, 32 (31) :3791-3794
[8]  
EMORY U, 1999, Patent No. 5914331
[9]   GENERAL-APPROACH TO HALOGENATED TETRAHYDROFURAN NATURAL-PRODUCTS FROM RED ALGAE OF THE GENUS LAURENCIA - TOTAL SYNTHESIS OF (+/-)-KUMAUSALLENE AND (+/-)-1-EPI-KUMAUSALLENE [J].
GRESE, TA ;
HUTCHINSON, KD ;
OVERMAN, LE .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2468-2477
[10]   A SHORT SYNTHESIS OF (+/-)-OXETANOCIN [J].
HAMBALEK, R ;
JUST, G .
TETRAHEDRON LETTERS, 1990, 31 (38) :5445-5448