Facile one-pot synthesis of resorcinol bis-C-glycosides possessing two identical sugar moieties

Synthesis

Volumn , Issue 17, 2006, Pages 2818-2824

  Yamauchi, Takahito ^a   Watanabe, Yukie ^a   Suzuki, Keisuke ^a   Matsumoto, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

bis C glycoside; Pluramycin; Rearrangement reactions; Resorcinol; Scandium(III) triflate

Indexed keywords

CATALYSIS; DERIVATIVES; SUGAR (SUCROSE);

BIS-C-GLYCOSIDE; PLURAMYCIN; REARRANGEMENT REACTIONS; RESORCINOL; SCANDIUM(III) TRIFLATE;

SYNTHESIS (CHEMICAL);

1 [2,6 DIHYDROXY 3,5 BIS(2,3,4 TRI O BENZYL BETA LEVO FUCOPYRANOSYL)PHENYL]ETHANONE; 1 [2,6 DIHYDROXY 3,5 BIS(2,3,4 TRI O BENZYL BETA LEVO RHAMNOPYRANOSYL)PHENYL]ETHANONE; 1,3 DIHYDROXY 2 IODO 4,6 BIS(2,3,4 TRI O BENZYL BETA LEVO FUCOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 IODO 4,6 BIS(2,3,4 TRI O BENZYL BETA LEVO RHAMNOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 METHYL 4,6 BIS(2 AZIDO 4 O BENZYL 2,3 DIDEOXY BETA DEXTRO ARABINO HEXOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 METHYL 4,6 BIS(2,3,4 TRI O BENZYL BETA LEVO FUCOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 METHYL 4,6 BIS(2,3,4 TRI O BENZYL BETA LEVO RHAMNOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 METHYL 4,6 BIS(3 AZIDO 2,4 DI O BENZYL 3,6 DIDEOXY BETA LEVO GALACTOPYRANOSYL)BENZENE; 1,3 DIHYDROXY 2 METHYL 4,6 BIS(3,4 DI O BENZYL 2 DEOXY BETA LEVO ARABINO HEXOPYRANOSYL)BENZENE; GLYCOSIDE; METHYL 2,6 DIHYDROXY 3,5 BIS(2,3,4 TRI O BENZYL BETA LEVO FUCOPYRANOSYL)BENZOATE; METHYL 2,6 DIHYDROXY 3,5 BIS(2,3,4 TRI O BENZYL BETA LEVO RHAMNOPYRANOSYL)BENZOATE; RESORCINOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS;

EID: 33748767410     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-942526     Document Type: Article

References (21)

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19. Another possible explanation is that bis-O-glycoside 5, once formed immediately rearranges to mono-O-mono-C-glycoside 7. However, this is unlikely since it was previously shown that protection of one hydroxyl group of a resorcinol derivative remarkably retards the O→C-glycoside rearrangement at the other hydroxyl; see ref. 4.
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