Solvent participation in a one-pot glycosylation strategy (SPOG)

Advanced Synthesis and Catalysis

Volumn 353, Issue 6, 2011, Pages 879-884

  Chao, Chin Sheng ^a   Yen, Yu Fang ^a   Hung, Wei Cheng ^a   Mong, Kwok Kong Tony ^a  

^a NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

low concentration glycosylation; nitriles; one pot process; reactivity based reaction; solvent participation

Indexed keywords

EID: 79955445336     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000888     Document Type: Article

References (45)

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42. [22a]). Moreover, the C-2 azide in 30 was a strongly deactivating function; thus, 30 is far less reactive than 29 in glycosylation, see:, T. K. Ritter, K-K. T. Mong, H. Liu, T. Nakatani, C.-H. Wong, Angew. Chem. 2003, 115, 4805-4808
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44. The chemical shifts of anomeric carbons of 32 were found at 100.6 (C-1‴), 102.0 (C-1″), 102.3 (C-1′) and 103.5 (C-1) ppm.
45. The yields of oligosaccharide 21, 22, 24, 28 and 32 ranged from 45 to 55%. From TLC examination, the reactions were relatively clean except for 22 and 24, wherein a disarmed building block 20 was used. Probably, building block 20 contains a C-2 benzoyl function that might cause some side reactions. The formation of truncated coupling products is possible as the first glycosylation generates small amount of thio-transfer product that can react with the acceptor. However, we have not isolated these products as they were minor components in reaction mixture.