487040-51-7

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 487040-50-6 5-azido-3,4-di-O-benzyl-5-deoxy-β-D-fructopyranose 
• 368452-24-8 5-azideo-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-sorbopyranose 
• 368452-06-6 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-β-L-sorbopyranose 
• 340969-76-8 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 487040-55-1 (2R,3R,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 476156-42-0 (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 909192-17-2 methyl (2S,3R)-2,3-dihydroxy-3-[(2'R,3'R,4'R,5'S)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propanoate 
• 909192-18-3 methyl (2R,3S)-2,3-dihydroxy-3-[(2'R,3'R,4'R,5'S)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propanoate 
• 909192-16-1 methyl (E)-3-[(2'R,3'R,4'R,5'S)-3',4'-dibenzyloxy-N-benzyloxycarbonyl-5'-tert-butyldiphenylsilyloxymethylpyrrolidin-2'-yl]propenoate 
• 909192-15-0 (2S,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 
• 909192-19-4 (1R,2S,5S,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one 
• 909192-23-0 (1S,2R,5S,6R,7R,7aR)-6,7-dibenzyloxy-5-tert-butyldiphenylsilyloxymethyl-1,2-dihydroxypyrrolizidin-3-one 
• 909192-21-8 (1R,2R,3S,6R,7R,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxypyrrolizidine 
• 909192-25-2 (1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxypyrrolizidine 
• 909192-22-9 (1R,2R,3S,6R,7R,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine 
• 909192-26-3 (1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine 
• 861872-76-6 (2R,3R,4R,5R)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine 

Relevant academic research and scientific papers

Polyhydroxylated pyrrolidines. Part 2: Highly stereoselective synthesis of partially protected DMDP derivatives from D-fructose

The readily available 3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 2 was straightforwardly transformed into 5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose 4, after treatment under modified Garegg's conditions followed by reaction of the resulting 3,4-di-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-L-sorbopyranose 3 with sodium azide in DMF. Cleavage of the acetonide of 4 to afford 6 followed by regioselective O-tert-butyldiphenylsilylation at C(1)OH afforded 7. Hydrogenation of 7 proceeded with high stereoselectivity yielding 3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-D-mannitol 1, confirmed by its O-desilylation to 8. Compound 1 was subjected to different N-protection reactions to afford the corresponding N-allyl (1a), N-benzyl (1b), and N-tert-butyloxycarbonyl (1c) derivatives.