140193-75-5

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 100-46-9 benzylamine 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 

Downstream Products

• 140193-70-0 1-O-trimethylsilyl-5-(N-benzyl-N-benzoxycarbonylamino)-2,3;6,7-di-O-isopropylidene-D-glycero-D-allo-heptofuranose 
• 140193-69-7 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone 
• 208649-02-9 (2S,3S)-3-hydroxypipecolic acid 
• 140193-68-6 5-(N-benzyl-N-benzoxycarbonylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enono-1,4-lactone 

Relevant academic research and scientific papers

Total synthesis of 1,5-dideoxy-1,5-iminoalditols

Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti, cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.