Synthesis of type 2 Lewis antigens via novel regioselective glycosylation of an orthogonally protected lactosamine diol derivative

Carbohydrate Research

Volumn 422, Issue , 2016, Pages 34-44

  Yamazaki, Yuji ^a   Sezukuri, Kyohei ^a   Takada, Junko ^a   Obata, Hiroaki ^a   Kimura, Shunsaku ^a   Ohmae, Masashi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Lewis y; Regioselective glycosylation; Sulfated Lewis x; The Heyns rearrangement; Type 2 Lewis antigens

Indexed keywords

ANTIGENS; CHEMICAL MODIFICATION; GLYCOSYLATION;

EFFICIENT SYNTHESIS; ETHYLENE OXIDES; LEWIS X; ORTHOGONAL SETS; PROTECTING GROUP; REACTION TEMPERATURE; REGIO-SELECTIVE; THE HEYNS REARRANGEMENT;

REGIOSELECTIVITY;

2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL 2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-2) 4,6 DI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTH; 2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL 2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-2) 4,6 TRI O ACETYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 ACETAMIDO 2 DEOXY BETA; 2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL 2,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL 2,4,6 TRI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL ALPHA LEVO FUCOPYRANOSYL (1-2) BETA DEXTRO GALACTOPYRANOSYL (1-4) [ALPHA LEVP FUCOPYRANOSYL (1-3)] 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [ALPHA LEVO FUCOPYRANOSYL (1-3)] 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSIDE; 2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-2) 4,6 DI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL LEVO FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYL TRICHLOROACETI; 2,4,6 TRI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERTBUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYLTRICHLOROACETIMIDATE; 2,4,6 TRI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERTBUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO DEXTRO GLUCOPYRANOSE; 4 METHOXYPHENYL 2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-2) 4,6 DI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOP; 4 METHOXYPHENYL 2,3,4 TRI O BENZYL ALPHA FUCOPYRANOSYL (1-2) 3 O BENZOYL 4,6 O BENZYLIDENE BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O BENZYL ALPHA FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 4 METHOXYPHENYL 2,4,6 TRI O ACETYL 3 O BENZOYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 6 TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 4 METHOXYPHENYL 3 O BENZOYL 4,6 O (4 METHOXYBENZYLIDENE) BETA DEXTRO GALACTOPYRANOSYL (1-4) 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 4 METHOXYPHENYL 3 O BENZOYL 4,6 O (4 METHOXYBENZYLIDENE) BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O BENZYL ALPHA FUCOPYRANOSYL (1-3)] 6 O TERT BUTYLDIPHENYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 4 METHOXYPHENYL 4,6 O (4 METHOXYBENZYLIDENE) BETA DEXTRO GALACTOPYRANOSYL (1-4) 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; 4 METHOXYPHENYL 4,6 O (4 METHOXYBENZYLIDENE) BETA DEXTRO GALACTOPYRANOSYL 6 O TERT TUTYLDIPHEYLSILYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSIDE; BLOOD GROUP ANTIGEN; LACTOSAMINE 3,2' DIOL DERIVATIVE; SODIUM {2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [ALPHA LEVO FUCOPYRANOSYL (1-3)] 2 ACETAMIDO 2 DEOXY 6 O SULFONATO BETA DEXTRO GLUCOPYRANOSIDE]; TRIETHYLAMMONIUM {2 [2 [2 (2 AZIDOETHOXY)ETHOXY]ETHOXY]ETHYL 2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL (1-4) [2,3,4 TRI O ACETYL ALPHA LEVO FUCOPYRANOSYL (1-3)] 2 ACETAMIDO 2 DEOXY 6 O SULFONATO BETA DEXTRO GLUCOPYRANOSIDE; TYPE 2 LEWIS ANTIGEN; UNCLASSIFIED DRUG; AMINOSUGAR; AZIDE; BLOOD GROUP LEWIS SYSTEM; GLYCOL; LACTOSAMINE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CHEMICAL MODIFICATION; CHEMICAL REACTION; CLICK CHEMISTRY; COLUMN CHROMATOGRAPHY; CYCLOADDITION; ENVIRONMENTAL TEMPERATURE; FUCOSYLATION; GLYCOSYLATION; HYDROGENATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTEIN SYNTHESIS; REGIOSELECTIVITY; TEMPERATURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

AMINO SUGARS; AZIDES; CHEMISTRY TECHNIQUES, SYNTHETIC; GLYCOLS; GLYCOSYLATION; KINETICS; LEWIS BLOOD-GROUP SYSTEM; STEREOISOMERISM;

EID: 85013110984     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2016.01.003     Document Type: Article

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