ENANTIOMERICALLY PURE 7-OXABICYCLO(2.2.1)HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .25. TOTAL ASYMMETRIC-SYNTHESIS OF 3-AMINO-3-DEOXY-L-TALOSE AND DERIVATIVES

被引：4

作者：

HUNENBERGER, P ^{[1
]}

ALLEMANN, S ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,CH-1005 LAUSANNE,SWITZERLAND

来源：

CARBOHYDRATE RESEARCH | 1994年 / 257卷 / 02期

关键词：

D O I：

10.1016/0008-6215(94)80034-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

(1R,2R,4R)-2-exo-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl (1S')-camphanate [(+)-1, Diels-Alder adduct of furan to 1-cyanovinyl (1S)-camphanate] was transformed with high stereoselectivity into (1R,2R,6R,7R)-4-phenyl-3,10-dioxa-5-azatricyclo[5.2.1.0(2,6)]dec-4-en-9-one [(+)-10]. Bromination of the corresponding (tert-butyl)dimethylsilyl enol ether [(-)-11], followed by Baeyer-Villiger oxidation and then alkaline methanolysis provided methyl 3-amino-1,5-anhydro-2-O,3-N-benzoyl-3-deoxy-alpha-L-talofuranuronate [(-)-17], the reduction of which gave 3-amino-1,5-anhydro-2-O,3-N-benzoyl-3-deoxy-alpha-L-talofuranose [(-)-19]. Treatment with aqueous HCl furnished 3-amino-3-deoxy-L-talose hydrochloride [(-)-2].

引用

页码：175 / 187

页数：13

共 20 条

[1] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .17. TOTAL, ASYMMETRIC-SYNTHESIS OF HEXOSES AND AZASUGARS BRANCHED AT C(5)
WAGNER, J
VOGEL, P
TETRAHEDRON, 1991, 47 (46) : 9641 - 9658
[2] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .12. HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF OCTOSES AND DERIVATIVES
JEGANATHAN, S
VOGEL, P
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03): : 1133 - 1142
[3] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES AS SYNTHETIC INTERMEDIATES .3. TOTAL SYNTHESIS OF D-RIBOSE AND L-RIBOSE DERIVATIVES
WAGNER, J
VIEIRA, E
VOGEL, P
HELVETICA CHIMICA ACTA, 1988, 71 (03) : 624 - 630
[4] OPTICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS NEW CHIRONS
VOGEL, P
FATTORI, D
GASPARINI, F
LEDRIAN, C
SYNLETT, 1990, (04) : 173 - 185
[5] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGAR) AS SYNTHETIC INTERMEDIATES .15. A NEW TOTAL SYNTHESIS OF D-THREO-L-TALO-OCTOSE
NEFF, DP
CHEN, YW
VOGEL, P
HELVETICA CHIMICA ACTA, 1991, 74 (03) : 508 - 516
[6] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES AS SYNTHETIC INTERMEDIATES .16. TOTAL ASYMMETRIC-SYNTHESIS OF 6-DEOXY-5-C-METHYL-D-RIBO-HEXOSE STRUCTURE IN AQUEOUS-SOLUTION
WAGNER, J
VOGEL, P
CARBOHYDRATE RESEARCH, 1991, 222 : 151 - 161
[7] REGIOSELECTIVE AND STEREOSELECTIVE THIOAMINATION OF 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES
ALLEMAN, S
VOGEL, P
SYNLETT, 1993, (10) : 801 - 802
[8] Synthesis of 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives and their screening for antimicrobial and antioxidant properties
Dhanapal, Ramu
Perumal, Paramasivan T.
Ramprasath, Chandrasekaran
Mathivanan, Narayanasamy
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (12) : 3599 - 3603
[9] ENANTIOMERICALLY PURE 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES (NAKED SUGARS) AS SYNTHETIC INTERMEDIATES .7. ACID-CATALYZED REARRANGEMENT OF 3-AZA-8-OXATRICYCLO[3.2.1.0/2,4]OCTAN-6-ONE ACETALS - HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF 3-AMINO-3-DEOXY-D-ALTROSE AND DERIVATIVES
NATIVI, C
REYMOND, JL
VOGEL, P
HELVETICA CHIMICA ACTA, 1989, 72 (05) : 882 - 891
[10] REACTION OF DODECACARBONYLTRIRUTHENIUM WITH 7-OXABICYCLO[2.2.1]HEPT-5-EN-2-YL DERIVATIVES - SYNTHESIS OF (MU-3-ETA-2-BENZYNE)-NONACARBONYLDIHYDRIDOTRIRUTHENIUM AND DERIVATIVES
BONFANTINI, E
VOGEL, P
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (19) : 1334 - 1335

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