CLEAVAGE OF VALIDOXYLAMINE A DERIVATIVES WITH N-BROMOSUCCINIMIDE - PREPARATION OF BLOCKED SYNTHONS USEFUL FOR THE CONSTRUCTION OF CARBA-OLIGOSACCHARIDES COMPOSED OF IMINO LINKAGES

被引:23
作者
OGAWA, S
NAKAJIMA, A
MIYAMOTO, Y
机构
[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Yokohama
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期
关键词
D O I
10.1039/p19910003287
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of validoxylamine A and several of its derivatives with N-bromosuccinimide proceeded through cleavage of the imino bonds to give rise to the synthetically useful blocked derivatives of valienamine and validamine, and the cyclohexanone and cyclohexenone derivatives. Some carbatrehalose derivatives were readily prepared by coupling of a pair of these compounds by reductive alkylation with sodium cyanoborohydride.
引用
收藏
页码:3287 / 3290
页数:4
相关论文
共 12 条
[1]  
ASANO N, 1988, 11TH JAP CARB S GIF, P111
[2]   STUDIES ON VALIDAMYCINS, NEW ANTIBIOTICS .5. DEGRADATION STUDIES [J].
HORII, S ;
IWASA, T ;
KAMEDA, Y .
JOURNAL OF ANTIBIOTICS, 1971, 24 (01) :57-&
[3]   UNSATURATED CYCLITOL PART OF NEW ANTIBIOTICS, VALIDAMYCINS [J].
KAMEDA, Y ;
HORII, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (12) :746-&
[4]  
KOHN A, 1985, LIEBIGS ANN CHEM, P775
[5]   SYNTHETIC STUDIES ON ANTIBIOTIC VALIDAMYCINS .13. TOTAL SYNTHESIS OF (+)-VALIDAMYCIN-A AND VALIDAMYCIN-E, AND RELATED-COMPOUNDS [J].
MIYAMOTO, Y ;
OGAWA, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :1013-1018
[6]   SYNTHETIC STUDIES ON THE VALIDAMYCINS .1. SYNTHESIS OF BETA-D-GLUCOPYRANOSYLVALIDAMINE - 1L-2-O-(BETA-D-GLUCOPYRANOSYL)-(1,3,4/2,6)-4-AMINO-6-HYDROXYMETHYL-1,2,3-CYCLOHEXANETRIOL [J].
OGAWA, S ;
SHIBATA, Y ;
CHIDA, N ;
SUAMI, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (02) :494-498
[7]   SYNTHETIC STUDIES ON ANTIBIOTIC VALIDAMYCINS .12. TOTAL SYNTHESIS OF (+)-VALIDAMYCIN-B AND (+)-VALIDOXYLAMINE-B [J].
OGAWA, S ;
MIYAMOTO, Y ;
NOSE, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (09) :2675-2680
[8]   SYNTHETIC STUDIES ON ANTIBIOTIC VALIDAMYCINS .11. SYNTHESIS OF VALIDAMYCIN A [J].
OGAWA, S ;
NOSE, T ;
OGAWA, T ;
TOYOKUNI, T ;
IWASAWA, Y ;
SUAMI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2369-2374
[9]   CLEAVAGE OF THE IMINO BONDS OF VALIDOXYLAMINE-A DERIVATIVES WITH N-BROMOSUCCINIMIDE [J].
OGAWA, S ;
MIYAMOTO, Y ;
NAKAJIMA, A .
CHEMISTRY LETTERS, 1989, (05) :725-728
[10]   TOTAL SYNTHESIS OF (+)-(1,2,3/4,5)-2,3,4,5-TETRAHYDROXYCYCLOHEXANE-1-METHANOL AND (+)-(1,3/2,4,5)-5-AMINO-2,3,4-TRIHYDROXYCYCLOHEXANE-1-METHANOL [(+)-VALIDAMINE] - X-RAY CRYSTAL-STRUCTURE OF (3S)-(+)-2-EXO-BROMO-4,8-DIOXATRICYCLO[4.2.1.O3,7]NONAN-5-ONE [J].
OGAWA, S ;
IWASAWA, Y ;
NOSE, T ;
SUAMI, T ;
OHBA, S ;
ITO, M ;
SAITO, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (04) :903-906