NEW CHIRAL BUILDING-BLOCKS AND THEIR APPLICATION TO THE CONSTRUCTION OF CHIRAL AMINOALCOHOLS - ENANTIOMERICALLY PURE CIS-3-MESYLOXY-4-HYDROXY AND TRANS-3-MESYLOXY-4-HYDROXY TETRAHYDROFURANS

被引：10

作者：

BORNER, A ^{[1
]}

HOLZ, J ^{[1
]}

KAGAN, HB ^{[1
]}

机构：

[1] UNIV PARIS 11,SYNTH ASYMETR LAB,CNRS,URA 1497,F-91405 ORSAY,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 33期

关键词：

D O I：

10.1016/S0040-4039(00)73971-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 3-mesyloxy-4-hydroxy tetrahydrofurans is described, starting from the chiral pool. The usefulness of these building blocks is illustrated by the synthesis of enantiomerically pure 3-amino-4-hydroxy-tetrahydrofurans.

引用

页码：5273 / 5276

页数：4

共 18 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] DARSTELLUNG DER STEREOISOMEREN DIHYDRO-SANTENE - DER VERLAUF DER KATALYTISCHEN HYDRIERUNG VON SANTEN [J].

ALDER, K ;

ROTH, W .

CHEMISCHE BERICHTE-RECUEIL, 1954, 87 (02) :161-167

[3] PREPARATION AND PHYSICAL PROPERTIES OF SULFUR COMPOUNDS RELATED TO PETROLEUM .6. ENDO-4,7-METHANO-CIS-2-THIAHYDRINDAN AND ENDO-4,7-ETHANO-CIS-2-THIAHYDRINDAN [J].

BIRCH, SF ;

HUNTER, NJ ;

MCALLAN, DT .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (09) :970-974

[4]

BORNER A, 1990, SYNTHESIS-STUTTGART, P573

[5]

BORNER A, 1990, PHARMAZIE, V45, P531

[6]

BORNER A, 1989, TETRAHEDRON LETT, V30, P929

[7] SYNTHESIS OF VARIOUS 3'-BRANCHED 2',3'-UNSATURATED PYRIMIDINE NUCLEOSIDES AS POTENTIAL ANTI-HIV AGENTS [J].

CZERNECKI, S ;

EZZITOUNI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7325-7328

[8] A GENERAL WAY, FROM L-ASCORBIC AND D-ISOASCORBIC ACIDS, TO HOMOCHIRAL ALPHA-HYDROXY, ALPHA,BETA-DIHYDROXY AND ALPHA,BETA-EPOXY-ALDEHYDES, USEFUL BUILDING-BLOCKS FOR THE SYNTHESIS OF LINEAR OXYGENATED FATTY-ACIDS METABOLITES [J].

GRAVIERPELLETIER, C ;

DUMAS, J ;

LEMERRER, Y ;

DEPEZAY, JC .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (08) :969-998

[9] THREITAN AND ERYTHRITAN AND THEIR REACTION WITH PERIODATE [J].

KLOSTERMAN, H ;

SMITH, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (21) :5336-5339

[10] CHIRAL ALPHA-HYDROXY-AND ALPHA,BETA-DIHYDROXY-ALDEHYDES FROM D-ISOASCORBIC AND L-ASCORBIC ACIDS - USEFUL PRECURSORS FOR THE SYNTHESIS OF FATTY-ACID METABOLITES [J].

LEMERRER, Y ;

GRAVIERPELLETIER, C ;

DUMAS, J ;

DEPEZAY, JC .

TETRAHEDRON LETTERS, 1990, 31 (07) :1003-1006

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