+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

Diastereoselective Reformatsky reaction of methyl 4-bromocrotonate with 1,2:5,6-di-O-isopropylidene-alpha-D-ribo-hexofuranos-3-ulose: application to novel bicyclic nucleosides

Diastereoselective Reformatsky reaction of methyl 4-bromocrotonate with 1,2:5,6-di-O-isopropylidene-alpha-D-ribo-hexofuranos-3-ulose: application to novel bicyclic nucleosides

Tetrahedron 60(45): 10269-10275

This paper describes an efficient synthetic route for novel bicyclic nucleosides. The stereochemistry of the targeted bicyclic nucleosides was successfully achieved by vinylogous Reformatsky reaction and ring closing metathesis reaction on a carbohydrate backbone. Copyright 2004 Elsevier Ltd.

(PDF emailed within 1 workday: $29.90)

Accession: 011951003

Download citation: RISBibTeXText

Related references

Synthesis of branched-chain sugar derivatives from 1,2;5,6-di-O-isopropylidene-alpha-D-ribo-hexofuranos-3-ulose and 1,2;4,5-di-O-isopropylidene-beta-D-erythro-2-hexulopyranos-3-ulose. Carbohydrate Research 329(4): 901-906, 2000

Large-scale preparation of D-allose: observations on the stereoselectivity of the reduction of 1,2:5,6-di-O-isopropylidene- -D-ribo-hexofuranos-3-ulose hydrate. Carbohydrate Research 24(1): 192-197, 1972

Reaction of d ribo hexos 3 ulose and of 1 2 5 6 di o iso propylidene alpha d ribo hexo 1 4 furanos 3 ulose 3 hydrate with methanol hydrogen chloride a preparation of d ribo 3 hexulose. Carbohydrate Research 16(2): 317-325, 1971

Methylation study of ribo nucleosides deoxy ribo nucleosides and 2' o methyl ribo nucleosides with tri methyl sulfonium hydroxide and tri methyl sulfonium iodide influence of the 2' hydroxy groups on the reactivity of the base moieties of ribo nucleosides. Journal of the Chemical Society Perkin Transactions I (12): 2787-2792, 1980

Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside. Carbohydrate Research 337(8): 663-672, 2002

Reaction of methyl 2 3 o isopropylidene 6 o p tolylsulfonyl alpha d lyxo hexo furanosid 5 ulose with tri ethylamine methanol. Carbohydrate Research 26(2): 297-303, 1973

(Z)-1,2:5,6-Di-O-isopropyl-idene-α-d-ribo-hexofuranos-3-ulose O-benzyl-oxime. Acta Crystallographica. Section E, Structure Reports Online 65(Pt 3): O633-O633, 2009

Properties and reactions of 1.2;5.6-di-O-isopropylidene-alpha-ribo-hexafurinos-3-ulose. Synthesis of D-gulose from D-glucose. Chemische Berichte 102(3): 1071-1075, 1969

Reaction of 1 2 5 6 di o isopropylidene alpha d ribohexofuranos 3 ulose benzoylhydrazone with acetic anhydride. Carbohydrate Research 163(1): 123-126, 1987

Nucleosides part 104 synthesis of 4 amino 5 d ribo furanosyl pyrimidine c nucleosides from 2 2 3 o isopropylidene 5 o trityl d ribo furanosyl acetonitrile. Journal of Organic Chemistry 42(4): 711-714, 1977

Reaction of derivatives of methyl 2,3-O-benzylidene-6-deoxy-alpha-L-mannopyranoside with butyllithium: synthesis of methyl 2,6-dideoxy-4-O-methyl-alpha-L-erythro-hexopyranosid-3-ulose. Carbohydrate Research 49: 305-314, 1976

Novel application of sugar borate complexation for separation of ribo nucleosides 2 deoxy ribo nucleosides and arabino nucleosides on cation exchange resin. Journal of Chromatography 148(2): 545-548, 1978

Silica gel-catalysed addition of methyl nitroacetate to 1,2:3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranose and 2,3-O-isopropylidene-D-glyceraldehyde: Crystal structure of methyl 7-acetamido-7-deoxy-1,2:3,4-di-O-isopropylidene-L-threo-alpha-D-galacto-octopyranuronate. Carbohydrate Research 271(1): 79-99, 1995

Reaction of derivatives of methyl 2 3 o benzylidene 6 deoxy alpha manno pyranoside with butyl lithium synthesis of methyl 2 6 dideoxy 4 o methyl alpha erythro hexo pyranosid 3 ulose. Carbohydrate Research 49: 305-314, 1976