188242-66-2

Upstream product

• 501-53-1 benzyl chloroformate 
• 188242-63-9 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-2-O-methanesulfonyl-5,6-dideoxy-D-allose dimethylacetal 
• 188242-60-6 benzyl (3R)-t-4,t-5-isopropylidenedioxy-c-6-dimethoxymethyl-r-3-methyl-1,2-oxazane-2-carboxylate 
• 188242-61-7 5-(benzyloxycarbonylamino)-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal 
• 173829-12-4 (3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 264234-39-1 5-amino-3,4-O-isopropylidene-5,6-dideoxy-D-allose dimethylacetal 
• 188242-64-0 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altrose dimethylacetal 

Downstream Products

• 264234-50-6 (2S,3S,4R,5R)-1-benzyloxycarbonyl-2-hydroxymethyl-3,4-isopropylidenedioxy-5-methylpyrrolidine 
• 264234-44-8 2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-allitol 
• 264234-42-6 2,5-(benzyloxycarbonylimino)-2,5,6-trideoxy-D-altritol 
• 637771-89-2 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-methylpyrrolidine-3,4-diol 
• 637771-89-2 (2S,3S,4R,5R)-3,4-dihydroxy-2-hydroxymethyl-5-methylpyrrolidine 
• 188242-67-3 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-allose 
• 264234-45-9 2,5-(benzyloxycarbonylimino)-3,4-O-isopropylidene-2,5,6-trideoxy-D-altritol 

Relevant academic research and scientific papers

Chiral 5-methyl-trihydroxypyrrolidines - Preparation from 1,2-oxazines and glycosidase inhibitory properties

Chemical transformations of chiral 1,2-oxazines 4, 5 gave the 2,5,6- trideoxy-2,5-imino D-alditols 12b, 13b in the D-altritol and D-talitol series, respectively. Basic aldehyde epimerisation led to the D-allitol isomer 15b. Compound 12b is a potent α-L-fucosidase and α-D-galactosidase inhibitor. (C) 2000 Elsevier Science Ltd.

Potent glycosidase inhibitors via hetero Diels-Alder reactions: Asymmetric synthesis of 5-methyl-trihydroxypyrrolidines

Some straightforward chemical transformations of oxazine diol 4, which was obtained from sorbaldehyde 2 by an asymmetric hetero Diels-Alder reaction followed by osmylation, led to the protected dihydroxypyrrolidine-aldehyde 8a and, after basic epimerisation, to 8b. Reduction of the aldehyde moiety and deprotection gave the potent glycosidase inhibitors 2,5,6-trideoxy-2,5-imino-D-altritol and D-allitol 9a and 9b.