Format

Send to

Choose Destination
Carbohydr Res. 2008 Jul 21;343(10-11):1819-23. doi: 10.1016/j.carres.2008.04.005. Epub 2008 Apr 7.

Rhodium(II)-catalyzed decomposition of 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose: diastereoselective ether formation.

Author information

1
Department of Chemistry, Youngstown State University, Youngstown, OH 44555, USA.

Abstract

Standard diazo transfer to 3-O-(2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-d-allofuranose (2), using p-acetamidobenzenesulfonyl azide (p-ABSA, 3) and DBU as base, provides the expected 3-O-(2-diazo-2-phenylacetyl)-1,2;5,6-di-O-isopropylidene-alpha-D-allofuranose (4) as an orange syrup in 49% isolated yield. Subsequent decomposition of 4 using Rh(2)(OAc)(4) yields ether 5 in a highly diastereoselective manner and in 58% isolated yield. The X-ray crystal structure of 5 proves that both newly produced stereocenters have the (S) configuration; the conformation of the ester group at O-3 of the furanose ring of 5 is used to discuss the possible cause of the observed stereoselectivity.

PMID:
18439572
DOI:
10.1016/j.carres.2008.04.005
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Elsevier Science
Loading ...
Support Center