1609168-89-9

Upstream product

• 1609168-90-2 (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(acetoxymethyl)-3-benzyloxy-4-acetoxypyrrolidine 
• 1429412-85-0 (R,R,R,R)-4-benzyloxy-5-[N-benzyl-N-(α-methylbenzyl)amino]-6-(triisopropylsilyloxy)hex-1-en-3-ol 
• 1429412-90-7 (R,R,R,R)-N⁽¹⁾-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4-hydroxy-5-(iodomethyl)pyrrolidine 

Downstream Products

• 1609168-92-4 (2R,3R,4R,5S)-N⁽¹⁾-benzyl-2,5-bis(hydroxymethyl)-3-benzyloxy-4-hydroxypyrrolidine hydrochloride 
• 132295-44-4 2,5-anhydro-2,5-imino-D-glucitol 

Relevant academic research and scientific papers

Asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP]

The asymmetric syntheses of 2,5-dideoxy-2,5-imino-d-glucitol [(+)-DGDP] and 1,2,5-trideoxy-1-amino-2,5-imino-d-glucitol [(+)-ADGDP] were achieved via the ring-closing iodoamination of an enantiopure bishomoallylic amine, followed by functionalisation of the resultant iodomethyl substituted pyrrolidine. In the case of (+)-DGDP, formation of the corresponding aziridinium ion followed by regioselective ring-opening with H2O gave the desired hydroxymethyl substituted pyrrolidine as a single diastereoisomer (>99:1 dr), with subsequent deprotection giving (+)-DGDP in good yield. Whereas in the case of (+)-ADGDP, displacement of iodide with NaN3 proved to be optimal, giving (+)-ADGDP in good yield after reduction and deprotection.