Use of polymers as protecting groups in organic synthesis. Preparation of partially substituted derivatives of D-glucose

Jean M.J. Fréchet*, Geneviève Pellé

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations


Two types of insoluble polystyrene resins bearing vinylbenzaldehyde units have been prepared and used with high efficiency as temporary protecting groups in the synthesis of 2,3 disubstituted derivatives of methyl α-D- glucopyranoside.

Original languageEnglish (US)
Pages (from-to)225-226
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number6
StatePublished - 1975
Externally publishedYes

Bibliographical note

Funding Information:
Another glucosidic com- ponent of the mixture (9) isolated in 15% yield contained only one benzyl group and could not be crystallized. Similar benzylation of (3)at room temperature with NaH and benzyl chloride in dimethylformamide or KOBu t and benzyl chloride in tetrahydrofuran produced better yields of (8) (30-40%), together with some monobenzylated product (9). The increase in yield observed in the last two benzylations is probably due to the better swelling proper- ties of dimethylformamide and tetrahydrofuran as com-pared to Me,SO. Thus, accessibility of the reactive sites is favoured in the better swelling agents and this results in a more complete benzylation. The fact that a monobenzyl derivative of (3)is obtained in the benzylations may reflect the difficulty of preparing anions on some of the less accessible sites of the resin where ion-ion repulsions may become very important, a fact illustrated by the difficulties experienced3 in the acid-base titrations of resins containing carboxylic acid functional groups. Financial support of the National Research Council of Canada is gratefully acknowledged. (Received, 9th December 1974; Corn. 1481.) 3 JI M. Fr6chet an; C. Schuerch, J. Amer. Chem. SOC.,1971, 93, 492. 4 K. W. Pepper, H. M. Paisley, and M. A. Young, J. Chem. SOC.,1953, 4097. 6D. J. Bell, J. Chem. SOC.,1934, 1177. I? K. Freudenberg and E. Plankenhorn, Bey., 1940, 73, 621.

ASJC Scopus subject areas

  • Molecular Medicine


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