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

✍ Scribed by Ogawa, Seiichiro ;Hirai, Keisuke ;Ohno, Masatsugu ;Furuya, Takashi ;Sasaki, Shin-Ichi ;Tsunoda, Hidetoshi

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Volume
1996
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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‐Glc__p__NAc‐(1→4)‐D‐Man__p__ (1) was synthesized.

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Synthesis of ether-linked octyl 5aЈ-carba-β-lactosaminide 3 substrate for human-milk α-(1Ǟ3/4)-fucosyltransferase and, interestingly, 5 is not. In addition, the imino-linked and -isolactosaminide 5 was carried out in seven steps, starting from the coupling products of 1,2-anhydro-5a-carba-congeners