Synthesis of D-erythro-Ceramide-1-phosphoinositol and Its Aminoglucosylated Derivative − Intermediates in GPI-Anchor Biosynthesis
✍ Scribed by Bernd Kratzer; Thomas G. Mayer; Richard R. Schmidt
- Publisher
- John Wiley and Sons
- Year
- 1998
- Tongue
- English
- Weight
- 624 KB
- Volume
- 1998
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and re-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite moval of the cyanoethyl group, to protected 2-azido-D-glucopyranosyl-α(1Ǟ6)-D-myo-inositol-1-phospho-ceramide (25) derivative 7 of 3-O-tert-butyldimethylsilyl-protected ceramide furnished the target molecule D-erythro-ceramide-1- which could be fully deprotected in two steps to afford the target molecule, the ceramide derivative of 2-amino-2-de-phosphoinositol (1). Reaction of O- (3,4,6-tri-O-acetyl-2azido-β-D-glucopyranosyl)trichloroacetimidate ( 20) with 3 oxy-D-glucopyranosyl-α(1Ǟ6)-D-myo-inositol-1-phosphate (2). gave exclusively α(1Ǟ6)-connected glycoside 21 which was converted into the 1α-O-unprotected derivative 24. Reaction