Synthesis of naturally occurring ld-Hepp containing disaccharides

G. J.P.H. Boons; R. Steyger; M. Overhand; G. A.van der Marel; J. H.van Boom

doi:10.1080/07328309108543968

Synthesis of naturally occurring ld-Hepp containing disaccharides

G. J.P.H. Boons, R. Steyger, M. Overhand, G. A.van der Marel, J. H.van Boom

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Diastereoselective hydroxymethylation of a suitably protected α -D-manno-hexodialdo-1, 5-pyranoside with the Grignard reagent derived from (phenyldimethylsilyl)methyl chloride gives, after additional protecting group manipulations, an easy access to one donor and two acceptors of LD-Hepp. The latter derivatives could be applied successfully for the preparation of the disaccharides α -D-GlcpN-(l-7)-L-α-D-Hepp-OMe and L-α-D-Hepp-(l-6)-L-α-D-Hepp-OMe.

Original language	English
Pages (from-to)	995-1007
Number of pages	13
Journal	Journal of Carbohydrate Chemistry
Volume	10
Issue number	6
DOIs	https://doi.org/10.1080/07328309108543968
Publication status	Published - 1 Jan 1991
Externally published	Yes

Funding

Financial support for this work was generously provided by the World Health Organisation. We wish to thank Mr A.W.M. Lefeber and Dr. C. Erkelens for recording the 'H and 13C NMR spectra.

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abstract = "Diastereoselective hydroxymethylation of a suitably protected α -D-manno-hexodialdo-1, 5-pyranoside with the Grignard reagent derived from (phenyldimethylsilyl)methyl chloride gives, after additional protecting group manipulations, an easy access to one donor and two acceptors of LD-Hepp. The latter derivatives could be applied successfully for the preparation of the disaccharides α -D-GlcpN-(l-7)-L-α-D-Hepp-OMe and L-α-D-Hepp-(l-6)-L-α-D-Hepp-OMe.",

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AU - Boons, G. J.P.H.

AU - Steyger, R.

AU - Overhand, M.

AU - der Marel, G. A.van

AU - Boom, J. H.van

PY - 1991/1/1

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N2 - Diastereoselective hydroxymethylation of a suitably protected α -D-manno-hexodialdo-1, 5-pyranoside with the Grignard reagent derived from (phenyldimethylsilyl)methyl chloride gives, after additional protecting group manipulations, an easy access to one donor and two acceptors of LD-Hepp. The latter derivatives could be applied successfully for the preparation of the disaccharides α -D-GlcpN-(l-7)-L-α-D-Hepp-OMe and L-α-D-Hepp-(l-6)-L-α-D-Hepp-OMe.

AB - Diastereoselective hydroxymethylation of a suitably protected α -D-manno-hexodialdo-1, 5-pyranoside with the Grignard reagent derived from (phenyldimethylsilyl)methyl chloride gives, after additional protecting group manipulations, an easy access to one donor and two acceptors of LD-Hepp. The latter derivatives could be applied successfully for the preparation of the disaccharides α -D-GlcpN-(l-7)-L-α-D-Hepp-OMe and L-α-D-Hepp-(l-6)-L-α-D-Hepp-OMe.

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Synthesis of naturally occurring ld-Hepp containing disaccharides

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