147455-52-5

Upstream product

• 501-53-1 benzyl chloroformate 
• 147455-51-4 C-[(R)-C-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-C-thiazol-2-yl]-methylamine 
• 147455-49-0 N-Benzyl-6-deoxy-6-(hydroxyamino)-1,2:3,4-O-isopropylidene-6-(2-thiazolyl)-β-L-glycero-D-galacto-1,5-hexopyranoside 
• 191997-37-2 (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 

Downstream Products

• 76951-87-6 1,2:3,4-di-O-isopropylidene-6--6-deoxy-L-glycero-α-D-galacto-heptopyranose 

Relevant academic research and scientific papers

Stereoselective Homologation-Amination of Aldehydes by Addition of Their Nitrones to C-2 Metalated Thiazoles - A General Entry to α-Amino Aldehydes and Amino Sugars

A general method for the homologation of aldehydes to α-amino aldehydes (aminohomologation) has been developed, which employs nitrones as iminium derivatives of the aldehydes.Key operations include a) the addition of a thiazole metalated at C-2 to the N-benzylnitrone derived from the aldehyde, b) the reductive dehydroxylation of the resultant thiazolyl N-benzylhydroxylamine, and c) the unmasking of the formyl group from the thiazole ring.The homologation sequence was studied by employing nitrones derived from various chiral polyalkoxy aldehydes and dialdoses.The addition of 2-lithiothiazole to these nitrones was syn-selective, whereas the reaction with the same nitrones precomplexed with Lewis acids was anti-selective.Hence, from each nitrone a pair of diastereoisomeric hydroxylamines was obtained.These compounds were then converted by the above sequence into α-epimeric α-amino aldehydes.Model elaborations of some of these products afforded the amino sugars D-glucosamine, D-mannosamine, D-nojirimycin, and advanced intermediates for the synthesis of destomic acid and lincosamine. - Keywords: amino aldehydes; aminohomologation; amino sugars; nitrones; thiazoles