A concise synthesis of tetrahydroxy-LCB, alpha-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks

Shun-Yuan Luo; Suvarn S Kulkarni; Chien-Hung Chou; Wei-Meen Liao; Shang-Cheng Hung

doi:10.1021/jo051518u

A concise synthesis of tetrahydroxy-LCB, alpha-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks

J Org Chem. 2006 Feb 3;71(3):1226-9. doi: 10.1021/jo051518u.

Authors

Shun-Yuan Luo¹, Suvarn S Kulkarni, Chien-Hung Chou, Wei-Meen Liao, Shang-Cheng Hung

Affiliation

¹ Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan.

PMID: 16438541
DOI: 10.1021/jo051518u

Abstract

The total syntheses of tetrahydroxy-LCB 1, alpha-galactosyl ceramide 2, and 1,4-dideoxy-1,4-imino-L-ribitol 3 via D-allosamine derivatives as common synthons are described here.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Arabinose / chemical synthesis*
Arabinose / chemistry
Galactosylceramides / chemical synthesis*
Galactosylceramides / chemistry
Glucosamine / analogs & derivatives*
Glucosamine / chemical synthesis
Glucosamine / chemistry
Hydroxylation
Imino Furanoses / chemical synthesis
Imino Furanoses / chemistry
Molecular Structure
Stereoisomerism
Sugar Alcohols / chemical synthesis*
Sugar Alcohols / chemistry

Substances

Galactosylceramides
Imino Furanoses
Sugar Alcohols
allosamine
alpha-galactosylceramide
1,4-dideoxy-1,4-iminoarabinitol
Arabinose
Glucosamine