THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY .29. THE PREPARATION OF INTERMEDIATES FOR THE SYNTHESIS OF 1D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE AND 2,4,5-TRISPHOSPHATE, 1,4-BISPHOSPHATE 5-PHOSPHOROTHIOATE, AND 4,5-BISPHOSPHATE 1-PHOSPHOROTHIOATE FROM 1D-3,6-DI-O-BENZYL-1,2-O-ISOPROPYLIDENE-MYO-INOSITOL

被引：20

作者：

DESAI, T ^{[1
]}

GIGG, J ^{[1
]}

GIGG, R ^{[1
]}

MARTINZAMORA, E ^{[1
]}

机构：

[1] NATL INST MED RES,LIPID & GEN CHEM LAB,LONDON NW7 1AA,ENGLAND

来源：

CARBOHYDRATE RESEARCH | 1994年 / 262卷 / 01期

关键词：

MYOINOSITOL PHOSPHATES; MYOINOSITOL PHOSPHOROTHIOATES; CHIRAL MYOINOSITOL DERIVATIVES; ALLYL ETHERS; CROTYL ETHERS;

D O I：

10.1016/0008-6215(94)84005-9

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：

The preparation of 1D-1,6-di-O-benzyl-2,5-di-O-p-methoxybenzyl-myo-inositol is described. This compound and 1D-3,6-di-O-benzyl-1,2-O-isopropylidene-myo-inositol were converted into 1D-1,3,6-tri-O-benzyl-myo-inositol which was phosphorylated to give an intermediate for the synthesis of 1D-myo-inositol 2,4,5-trisphosphate. 1D-3,6-Di-O-benzyl 1,2-O-isopropylidene-myo-inositol was converted into 1D-2,3,6-tri-O-benzyl-myo-inositol (an intermediate for the synthesis of 1D-myo-inositol 1,4,5-trisphosphate) and 1D-2,3,6-tri-O-benzyl-1-O-p-methoxybenzyl-myo-inositol (an intermediate for the synthesis of the 1-phosphorothioate analogue of 1D-myo-inositol 1,4,5-trisphosphate). 1D-3,6-Di-O-benzyl-1,2-O-isopropylidene-myo-inositol was also converted into 1D-2,3,6-tri-O-benzyl-5-O-p-methoxybenzyl[and -5-O(cis-prop-1-enyl)]-myo-inositol both of which are intermediates for the synthesis of the 5-phosphorothioate analogue of 1D-myo-inositol 1,4,5-trisphosphate. The synthesis of 1D-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) 5-(dibenzyl phosphorothioate) from 1D-2,3,6-tri-O-benzyl-myo-inositol 1,4-bis(dibenzyl phosphate) is described.

引用

页码：59 / 77

页数：19

共 33 条

[1] ACTIVATION OF CA2+ ENTRY INTO ACINAR-CELLS BY A NON-PHOSPHORYLATABLE INOSITOL TRISPHOSPHATE [J].

BIRD, GS ;

ROSSIER, MF ;

HUGHES, AR ;

SHEARS, SB ;

ARMSTRONG, DL ;

PUTNEY, JW .

NATURE, 1991, 352 (6331) :162-165

[2] THE PARA-METHOXYBENZYL GROUP AS PROTECTIVE GROUP OF THE ANOMERIC CENTER - SELECTIVE CONVERSIONS OF HYDROXY-GROUPS INTO BROMO GROUPS IN PARA-METHOXYBENZYL 2-DEOXY-2-PHTHALIMIDO-BETA-D-GLUCOPYRANOSIDE [J].

CLASSON, B ;

GAREGG, PJ ;

SAMUELSSON, B .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (05) :419-422

[3] SYNERGISTIC CONTROL OF CA2+ MOBILIZATION IN PERMEABILIZED MOUSE L1210 LYMPHOMA-CELLS BY INOSITOL 2,4,5-TRISPHOSPHATE AND INOSITOL 1,3,4,5-TETRAKISPHOSPHATE [J].

CULLEN, PJ ;

IRVINE, RF ;

DAWSON, AP .

BIOCHEMICAL JOURNAL, 1990, 271 (02) :549-553

[4]

CUNNINGHAM J, 1964, TETRAHEDRON LETT, P1191

[5] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .26. THE PREPARATION OF INTERMEDIATES FOR THE SYNTHESIS OF 1D-MYO-INOSITOL 1,4,5-TRISPHOSPHATE, A 2ND MESSENGER FOR SIGNAL TRANSDUCTION IN CELLS [J].

DESAI, T ;

GIGG, J ;

GIGG, R ;

PAYNE, S ;

PENADES, S .

CARBOHYDRATE RESEARCH, 1992, 234 :1-21

[6] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE CHEMISTRY .24. THE PREPARATION AND PHOSPHORYLATION OF 2,5-DI-O-BENZYL-MYO-INOSITOL AND 1D-2,6-DI-O-BENZYL-MYO-INOSITOL [J].

DESAI, T ;

GIGG, J ;

GIGG, R ;

PAYNE, S .

CARBOHYDRATE RESEARCH, 1992, 228 (01) :65-79

[7] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .22. THE SYNTHESIS AND RESOLUTION OF (+/-)-1,5,6-TRI-O-BENZYL-MYO-INOSITOL [J].

DESAI, T ;

FERNANDEZMAYORALAS, A ;

GIGG, J ;

GIGG, R ;

PAYNE, S .

CARBOHYDRATE RESEARCH, 1990, 205 :105-123

[8] THE SYNTHESIS AND RESOLUTION OF (+/-)-1,4-DI-O-BENZYL-2,3-O-ISOPROPYLIDENE-MYO-INOSITOL [J].

DESAI, T ;

GIGG, J ;

GIGG, R ;

MARTINZAMORA, E ;

SCHNETZ, N .

CARBOHYDRATE RESEARCH, 1994, 258 :135-144

[9] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .25. THE PREPARATION, RESOLUTION, AND PHOSPHORYLATION OF SOME BENZYL ETHERS OF MYOINOSITOL - INTERMEDIATES FOR THE SYNTHESIS OF MYOINOSITOL PHOSPHATES OF THE PHOSPHATIDYLINOSITOL CYCLE [J].

DESAI, T ;

GIGG, J ;

GIGG, R ;

PAYNE, S .

CARBOHYDRATE RESEARCH, 1992, 225 (02) :209-228

[10] THE ALLYL GROUP FOR PROTECTION IN CARBOHYDRATE-CHEMISTRY .27. THE PREPARATION OF PHOSPHORYLATED INTERMEDIATES FOR THE SYNTHESIS OF RACEMIC AND CHIRAL MYOINOSITOL 1,4,5-TRISPHOSPHATE AND ITS PHOSPHOROTHIOATE ANALOGS [J].

DESAI, T ;

FERNANDEZMAYORALAS, A ;

GIGG, J ;

GIGG, R ;

PAYNE, S .

CARBOHYDRATE RESEARCH, 1992, 234 :157-175

← 1 2 3 4 →