Synthesis of S-linked thiooligosaccharide analogues of Nod factors: Synthesis of new protected thiodisaccharide and thiotrisaccharide intermediates

Carbohydrate Research

Volumn 338, Issue 13, 2003, Pages 1369-1379

  Morais, Latino Loureiro ^a   Bennis, Khalil ^a   Ripoche, Isabelle ^a   Liao, Liang ^b   Auzanneau, France Isabelle ^b   Gelas, Jacques ^a  

^a Lab Chim Heterocycles/des Glucides   (France)

^b UNIVERSITY OF GUELPH   (Canada)

Author keywords

Analogues; Glycosylation; Nodulation factors; Thiooligosaccharides

Indexed keywords

CATALYSIS; SILICA GEL; SYNTHESIS (CHEMICAL);

NODULATION FACTORS;

CARBOHYDRATES;

1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY 4 O TRIFLUOROMETHANESULFONYL BETA DEXTRO GALACTOPYRANOSIDE; 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY 4 O TRIFLUOROMETHANESULFONYL BETA DEXTRO GLUCOPYRANOSIDE; 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GALACTOPYRANOSIDE; 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GLYCOPYRANOSIDE; 1,6 ANHYDRO 2 AZIDO 3,4 DI O BENZOYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSE; 1,6 DI O ACETYL 2 AZIDO 3,4 DI O BENZOYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSE; 1,6 DI O ACETYL 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSE; 2 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 PSEUDOTHIOUREA; 3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY 1 THIO BETA DEXTRO GLUCOPYRANOSE; 4 (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 1,6 DI O ACETYL 2 AZIDO 3 O BENZOYL 2 DEOXY 4 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSIDE; 4 (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 6 O ACETYL 2 AZIDO 3 O BENZOYL 2 DEOXY 4 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSE; 4 (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 6 O ACETYL 2 AZIDO 3 O BENZOYL 2 DEOXY 4 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETIMIDATE; 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO BETA DEXTRO GLUCOPYRANOSIDE; 4 O (6 O ACETYL 2 AZIDO 3,4 DI O BENZOYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSYL) 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 4 O (6 O ACETYL 2 AZIDO 3,4 DI O BENZYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSYL) 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 4 O [6 O ACETYL 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO ALPHA DEXTRO GLUCOPYRANOSYL] 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 4 O [6 O ACETYL 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO BETA DEXTRO GLUCOPYRANOSYL] 1,6 ANHYDRO 2 AZIDO 3 O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 6 O ACETYL 2 AZIDO 3,4 DI O BENZOYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSE; 6 O ACETYL 2 AZIDO 3,4 DI O BENZOYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETIMIDATE; 6 O ACETYL 2 AZIDO 3,4 DI O BENZYL 2 DEOXY ALPHA,BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETIMIDATE; 6 O ACETYL 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO ALPHA DEXTRO GLUCOPYRANOSYL TRICHLOROACETIMIDATE; 6 O ACETYL 4 (3,4,6 TRI O ACETYL 2 BENZYLOXYCARBONYLAMINO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) 2 AZIDO 3 O BENZYL 2 DEOXY 4 THIO ALPHA,BETA DEXTRO GLUCOPYRANOSE; CARBOHYDRATE DERIVATIVE; CHITINASE; DISACCHARIDE; SILICA GEL; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEVICE; GLYCOSYLATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTECTION; REACTION ANALYSIS; SEPARATION TECHNIQUE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038542995     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00149-6     Document Type: Article

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