Rational Design of Benzyl-Type Protecting Groups Allows Sequential Deprotection of Hydroxyl Groups by Catalytic Hydrogenolysis

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4172-4173

  Gaunt, Matthew J ^a   Yu, Jinquan ^a   Spencer, Jonathan B ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001325114     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980823v     Document Type: Article

References (15)

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12. f = 0.26) to afford methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside as a colorless oil (0.125 g, 90%).
13. To assess the stability of the protecting group, ether 10 was subjected to a range of chemical conditions. The NAP group was stable in acidic and basic solutions and to organometallics such as methyl magnesium bromide and DIBAL-H. The ether shows partial decomposition in n-butyllithium at 30°C.
14. (a) Evans, D. A.; Trotter, B. W.; Cote, B.; Coleman, P. J.; Dias, L. C.; Tyler, A. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 2744.
15. (b) Hayward, M. M.; Roth, R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.; Kishi, Y. Angew. Chem., Int. Ed. Engl. 1998, 37, 192.