Pseudosugars, 37. Preparation of Versatile Intermediates for Ether-Linked 5a-Carba Oligosaccharides: Synthesis of 5a-Carba-β-D-GlcpNAc-(1→4)-D-Manp

Autor:	Shin-ichi Sasaki, Masatsugu Ohno, Hidetoshi Tsunoda, Keisuke Hirai, Takashi Furuya, Seiichiro Ogawa
Rok vydání:	2006
Předmět:	chemistry.chemical_classification Ketone Pseudosugars Chemistry Stereochemistry Organic Chemistry Disaccharide Ether General Chemistry chemistry.chemical_compound Organic chemistry Physical and Theoretical Chemistry Sugar Derivative (chemistry)
Zdroj:	Liebigs Annalen. 1996:673-677
ISSN:	1099-0690 0947-3440
DOI:	10.1002/jlac.199619960505
Popis:	Coupling of 1,2-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose (3) with 1,6-anhydro-2,3-O-isopropylidene-β-D-mannopyranose (4) afforded a 5a′-carba disaccharide derivative linked by an ether bridge with α-manno configuration. This compound 5 was transformed into three stereoisomers in regard to the configurations at C-1′ and C-2′. Thus, the free 2′-hydroxyl group was oxidized, and the resulting ketone 8 was isomerized at C-1′ to 11 by treatment with potassium tert-butoxide. Reduction of the ketones 8 and 11 with l-selectride afforded selectively the synthetic useful intermediate ether-linked 5a′-carba disaccharides 9, 12, and 14 with α-gluco, β-gluco, and β-manno configurations, respectively. 5a-Carba sugar analog 2 of biologically interesting disaccharide β-D-GlcpNAc-(14)-D-Manp (1) was synthesized.
Databáze:	OpenAIRE
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