Linked Life Data

6171351

Source:http://linkedlifedata.com/resource/pubmed/id/6171351

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
1982-2-12
pubmed:abstractText
An approach has been developed for the rapid synthesis of benzyl 2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-beta-D-glucopyranoside (5). Disaccharide 5 was per(trimethylsilyl)ated, to provide the fully protected trimethylsilyl (Me3Si) derivative which, on treatment with pyridine-acetic anhydride-acetic acid for 2 days, gave the disaccharide derivative having O-acetyl groups selectively at the primary positions and Me3Si groups at the secondary positions. The latter groups were readily cleaved by treatment with aqueous acetic acid in methanol, to afford benzyl 2-acetamido-6-O-acetyl-3-O-(6-O-acetyl-beta-D-galactopyranosyl)-2-deoxy-beta-D- glucopyranoside, which, is isopropylidenation, gave the desired, key intermediate 9, having two hydroxyl groups free. Condensation of 9 with 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl bromide, under catalysis by halide ion, afforded the tetrasaccharide derivative, from which the title tetrasaccharide was obtained by systematic removal of the protecting groups. The structure of the final product, and of various other intermediates, was established by 1H- and 13C-n.m.r. spectroscopy.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Oct
pubmed:issn
0008-6215
pubmed:author
pubmed:issnType
Print
pubmed:day
16
pubmed:volume
96
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
231-9
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
1981
pubmed:articleTitle
The chemical synthesis of O-alpha-L-fucopyranosyl-(1 goes to 2)-O-beta-D-galactopyranosyl-(1 goes to 3)-O-[alpha-L-fucopyranosyl-(1 goes to 4)]-2-acetamido-2-deoxy-D-glucopyranose, the Lewis b blood-group antigenic determinant.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S.