COMMERCIAL SYNTHESIS OF ALPHA-D-CELLOBIOSYL BROMIDE HEPTAACETATE

被引:6
作者
GOGGIN, KD [1 ]
HAMMEN, PD [1 ]
KNUTSON, KL [1 ]
LAMBERT, JF [1 ]
WALINSKY, SW [1 ]
WATSON, HA [1 ]
机构
[1] PFIZER INC,DIV CENT RES,GROTON,CT 06340
关键词
ALPHA-D-CELLOBIOSYL BROMIDE HEPTAACETATE; ACETOBROMO-ALPHA-D-CELLOBIOSE; HBR BROMINATION OF ALPHA-CELLOBIOSE OCTAACETATE;
D O I
10.1002/jctb.280600305
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
A detailed commercial process for the synthesis and purification of the activated disaccharide, alpha-D-cellobiosyl bromide heptaacetate (1) was developed. Reaction Of alpha-D-cellobiose octaacetate (CBO) with HBr in glacial acetic acid or in glacial acetic acid/methylene chloride combination affords alpha-D-cellobiosyl bromide heptaacetate in high yield and excellent quality. Process variables such as reaction solvent, reaction time, reaction temperature, HBr stoichiometry, isolation methods and product purification options were optimized for large-scale synthesis. Alpha-D-cellobiosyl bromide heptaacetate was successfully prepared in a commercial manufacturing plant.
引用
收藏
页码:253 / 256
页数:4
相关论文
共 16 条
[1]   DEOXY-SUGARS .5. A REINVESTIGATION OF THE GLYCAL METHOD FOR THE SYNTHESIS OF 2-DEOXY-D-RIBOSE AND 2-DEOXY-L-RIBOSE [J].
DERIAZ, RE ;
OVEREND, WG ;
STACEY, M ;
TEECE, EG ;
WIGGINS, LF .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JUL) :1879-1883
[2]   PREPARATION OF GLYCOSYL HALIDES UNDER NEUTRAL CONDITIONS [J].
ERNST, B ;
WINKLER, T .
TETRAHEDRON LETTERS, 1989, 30 (23) :3081-3084
[3]   Some derivatives of milk sugars and the maltose and two new glucosides. [J].
Fischer, E ;
Fischer, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1910, 43 :2521-2536
[4]   THE REACTION OF TRIBENZOYL-BETA-D-ARABINOPYRANOSYL BROMIDE AND TRIBENZOYL-ALPHA-D-XYLOPYRANOSYL BROMIDE WITH METHANOL [J].
FLETCHER, HG ;
HUDSON, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (09) :4173-4177
[5]  
Freudenberg K, 1932, LIEBIGS ANN CHEM, V494, P63
[6]   DRUG GLYCOSIDES - POTENTIAL PRODRUGS FOR COLON-SPECIFIC DRUG DELIVERY [J].
FRIEND, DR ;
CHANG, GW .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (01) :51-57
[7]   TRIMETHYLSILYL BROMIDE AS A MILD, STEREOSELECTIVE ANOMERIC BROMINATING AGENT [J].
GILLARD, JW ;
ISRAEL, M .
TETRAHEDRON LETTERS, 1981, 22 (06) :513-516
[8]  
HIGASHI K, 1991, CHEM PHARM BULL, V39, P2502
[9]   A SIMPLIFIED, ONE-POT PREPARATION OF ACETOBROMOSUGARS FROM REDUCING SUGARS [J].
KARTHA, KPR ;
JENNINGS, HJ .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1990, 9 (05) :777-781
[10]  
Malinow M. R., 1986, US Patent, Patent No. [4,602,005, 4602005]