Intramolecular benzyl protection delivery: a practical synthesis of DMDP and DGDP from D-fructose.
[reaction: see text] A two-step protection of 1,2-diols as the corresponding o-xylylene cyclic ethers, involving an intramolecular ring-closing O-benzylation reaction, has been developed to overcome the problems associated to regioselective benzylation reactions. The strategy has been applied to the high-yielding synthesis of the pyrrolidine glycosidase inhibitors DMDP and DGDP.
García-Moreno
M Isabel
MI
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Spain.
Aguilar
Matilde
M
Ortiz Mellet
Carmen
C
García Fernández
José M
JM
D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050112:Imino Pyranoses / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D013012:Sorbitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
C513881:2,5-dideoxy-2,5-imino-D-glucitol; C494911:2,5-dideoxy-2,5-imino-D-mannitol; D004988:Ethers, Cyclic; D050112:Imino Pyranoses; D005632:Fructose; D008353:Mannitol; D013012:Sorbitol; D006026:Glycoside Hydrolases