Selective protections on 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-beta-D-glucopyranose.
Regioselective monoacetylation of 2-allyloxycarbonylamino-1,6-anhydro-2-deoxy-beta-D-glucopyranose (1) gave a mixture of 3-O-acetyl and 4-O-acetyl derivatives, the structures of which were established by two-dimensional, phase-sensitive NOESY and confirmed by chemical proofs. The benzylation of 1, on the other hand, led to 2-allyloxycarbonylamino-1,6-anhydro-3,4-di- (5) or 2-allyloxycarbonylamino-1,6-anhydro-2-N-benzyl-3,4-di-O-benzyl-2-d eoxy-beta-D- glucopyranose (10). The regioselective cleavage of 5 with titanium tetrachloride gave the expected 3-O-benzyl derivative, the structure of which was ascertained by chemical proofs; the same reaction performed on 10 led to the opening of the anhydro ring to afford 3-benzyl-[3,4-di-O-benzyl-1,2-dideoxy-alpha-D-glucopyrano]-[2,1-d] -2- oxazolidone.
Bouali
A
A
Laboratoire Chimie Organique II, U.R.A. C.N.R.S. 463. Université Claude Bernard Lyon, Villeurbanne, France.
Boullanger
P
P
Lafont
D
D
Fenet
B
B
D002240:Carbohydrate Sequence; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis
D009844:Oligosaccharides; C076317:2-allyloxycarbonylamino-1,6-anhydro-2-deoxyglucopyranose; D003847:Deoxyglucose; D005944:Glucosamine