Synthesis and theoretical study of azido and amino inositol derivatives from L-quebrachitol

被引:15
作者
De Almeida, MV
Figueiredo, RM
Dos Santos, HF
Da Silva, AD
De Almeida, WB [1 ]
机构
[1] Univ Fed Minas Gerais, ICEx, Dept Quim, Lab Quim Computac & Modelagem Mol, BR-31270901 Belo Horizonte, MG, Brazil
[2] Univ Fed Juiz de Fora, ICE, Dept Quim, Juiz De Fora, MG, Brazil
关键词
D O I
10.1016/S0040-4039(01)00326-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some azido and amino inositol derivatives were synthesised from L-quebrachitol. The reaction between the mesylated compound and sodium azide was studied experimentally. Ab initio quantum mechanical calculations were carried out for this process to better understand the reaction mechanism. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2767 / 2769
页数:3
相关论文
共 15 条
[1]   A convenient approach to the aminocyclitol fragment of pancratistatin from 7-oxanorbornenes [J].
Acena, JL ;
Arjona, O ;
Iradier, F ;
Plumet, J .
TETRAHEDRON LETTERS, 1996, 37 (01) :105-106
[2]  
ARJONA O, 1995, TETRAHEDRON LETT, V8, P6659
[3]  
BRUNN G, 1994, CANCER CHEMOTH PHARM, V35, P71, DOI 10.1007/s002800050195
[4]   TOTAL SYNTHESIS OF METHOXYHYGROMYCIN AND ITS 5-EPIMER [J].
CHIDA, N ;
NAKAZAWA, K ;
OHTSUKA, M ;
SUZUKI, M ;
OGAWA, S .
CHEMISTRY LETTERS, 1990, (03) :423-426
[5]   Ab initio study of solvated molecules: A new implementation of the polarizable continuum model [J].
Cossi, M ;
Barone, V ;
Cammi, R ;
Tomasi, J .
CHEMICAL PHYSICS LETTERS, 1996, 255 (4-6) :327-335
[6]   An efficient synthesis of protected 2-deoxy-streptamine and analogues [J].
da Silva, ET ;
Le Hyaric, M ;
Machado, AS ;
de Almeida, MV .
TETRAHEDRON LETTERS, 1998, 39 (37) :6659-6662
[7]   A theoretical study of the interaction of anhydrotetracycline with Al(III) [J].
De Almeida, WB ;
Dos Santos, HF ;
Zerner, MC .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1998, 87 (09) :1101-1108
[8]   MINOSAMINOMYCIN, A NEW ANTIBIOTIC CONTAINING MYO-INOSAMINE [J].
HAMADA, M ;
KONDO, S ;
YOKOYAMA, T ;
MIURA, K ;
IINUMA, K ;
YAMAMOTO, H ;
MAEDA, K ;
TAKEUCHI, T ;
UMEZAWA, H .
JOURNAL OF ANTIBIOTICS, 1974, 27 (01) :81-83
[9]   EXPEDIENT SYNTHETIC ROUTES TO [H-3] D-3-AZIDO-3-DEOXY-MYO-INOSITOL AND D-3-AZIDO-3-DEOXY-MYO-INOSITOL 2,4,5-TRISPHOSPHATE [J].
KOZIKOWSKI, AP ;
FAUQ, AH ;
POWIS, G ;
KURIAN, P ;
CREWS, FT .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) :362-364
[10]   EFFICIENT SYNTHETIC ROUTES TO FLUORINATED ISOSTERES OF INOSITOL AND THEIR EFFECTS ON CELLULAR GROWTH [J].
KOZIKOWSKI, AP ;
FAUQ, AH ;
POWIS, G ;
MELDER, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4528-4531