RETENTION AND APPARENT INVERSION DURING AZIDE DISPLACEMENT OF ALPHA-TRIFLATES OF 1,5-LACTONES

被引:42
作者
BRUCE, I [1 ]
FLEET, GWJ [1 ]
GIRDHAR, A [1 ]
HARALDSSON, M [1 ]
PEACH, JM [1 ]
WATKIN, DJ [1 ]
机构
[1] CHEM CRYSTALLOG LAB,OXFORD OX1 3PD,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)97581-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of azide ion with 2-O-trifluoromethanesulphonates of both 34:67-di-O-isopropylidene-D-glycero-D-talo-hepton-0-15-lactone and of 34;67-di-O-isopropylidene-D-glycero-D-galacto-heptono-1-5-lactone give predominantly 2-azido-2-deoxy-3 4:6 7-di-O-isopropylidene-D-glycero-D-galacto 5-lactone initially which then isomerises under the reaction conditions to 2-azido-2-deoxy-34:67-di-O-isopropylidene-Dglycerol-D-talo-heptono-1 X-ray crystal structure analyses of 34;67-di-O-isopropylidene-D-glyceroD-1-talo-heptono-1 5-lactone. and 2-azido-2-deoxy-3 4:6 7-di-O-isopropylidene-D-glycero-D-talo-heptono-15-lactone are reported. © 1990.
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页码:19 / 32
页数:14
相关论文
共 18 条
[1]  
[Anonymous], 1974, INT TABLES XRAY CRYS, VIV
[2]   SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET [J].
BAIRD, PD ;
DHO, JC ;
FLEET, GWJ ;
PEACH, JM ;
PROUT, K ;
SMITH, PW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1785-1791
[3]   SYNTHESIS OF 2S,4S,5S-DIHYDROXYPIPECOLIC ACID AND BULGECININE [2S,4S,5R-4-HYDROXY-5-(HYDROXYMETHYL)PROLINE] FROM D-GLUCURONOLACTONE - A STRATEGY FOR THE SYNTHESIS OF 2S,4S-4-HYDROXY-ALPHA-AMINO ACIDS [J].
BASHYAL, BP ;
CHOW, HF ;
FLEET, GWJ .
TETRAHEDRON, 1987, 43 (02) :423-430
[4]   THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE [J].
BASHYAL, BP ;
CHOW, HF ;
FELLOWS, LE ;
FLEET, GWJ .
TETRAHEDRON, 1987, 43 (02) :415-422
[5]  
DHO JC, 1986, TETRAHEDRON LETT, V27, P5307
[6]  
FELLOWS LE, 1988, TETRAHEDRON, V44, P5959
[7]   ON ENANTIOMORPH-POLARITY ESTIMATION [J].
FLACK, HD .
ACTA CRYSTALLOGRAPHICA SECTION A, 1983, 39 (NOV) :876-881
[8]   PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND MANNONOLACTAM FROM L-GULONOLACTONE - SYNTHESIS OF L-DEOXYMANNOJIRIMYCIN AND L-MANNONOLACTAM FROM D-GULONOLACTONE [J].
FLEET, GWJ ;
RAMSDEN, NG ;
WITTY, DR .
TETRAHEDRON, 1989, 45 (01) :319-326
[9]   THE PREPARATION OF HIGHER-CARBON SUGARS FROM D-MANNOSE INCLUDING CRYSTALLINE D-MANNO-L-MANNO-OCTOSE [J].
KARABINOS, JV ;
HANN, RM ;
HUDSON, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (17) :4320-4324
[10]  
KITE GC, 1988, TETRAHEDRON LETT, V29, P6486