Simple synthesis of D-erythro- and L-erythro-D-gluco-octoses

Authors
Jarosz, S Skora, S Kosciolowska, I
Citation
S. Jarosz et al., Simple synthesis of D-erythro- and L-erythro-D-gluco-octoses, POL J CHEM, 73(11), 1999, pp. 1797-1802
Citations number
10
Categorie Soggetti
Chemistry
Journal title
POLISH JOURNAL OF CHEMISTRY
ISSN journal
01375083 → ACNP
Volume
73
Issue
11
Year of publication
1999
Pages
1797 - 1802
Database
ISI
SICI code
0137-5083(199911)73:11<1797:SSODAL>2.0.ZU;2-D
Abstract
Synthesis of the previously unknown methyl 2,3,4-tri-O-benzyl-L-erythro-bet a-D-gluco- and D-elythro-alpha-D-gluco-oct-1,5-pyranosides (1 and 2) was ac complished on two independent routes via either cis-hydroxylation of stereo isomeric 6-C-vinyl-L-glycero-beta-D-gluco- and D-glycero-alpha-D-gluco-pyra nosides (9 and 10 respectively) or by epoxi dation (following by the openin g of the three membered ring) of methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-oct- 6(E)-eno-alpha-D-gluco-pyranoside (11).