158705-81-8

Basic information

• Product Name: 5-amino-1,5,6-trideoxy-D-allose
• CAS NO: 158705-81-8
• Molecular Weight: 147.174
• Mol File: 158705-81-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-amino-1,5,6-trideoxy-D-allose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1,5,6-trideoxy-D-allose(158705-81-8)
• EPA Substance Registry System: 5-amino-1,5,6-trideoxy-D-allose(158705-81-8)

Safety Data

• Hazardous Substances Data: 158705-81-8(Hazardous Substances Data)

Upstream product

• 197294-81-8 (3R,6R)-6-Dimethoxymethyl-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester 
• 197294-89-6 (2R,3R,4R,5R)-5-Amino-1,1-dimethoxy-hexane-2,3,4-triol 
• 173829-12-4 (3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 110261-62-6 benzyl trans-6-(dimethoxymethyl)-3,6-dihydro-3-methyl-2H-1,2-oxazine-2-carboxylate 
• 72908-59-9 sorbaldehyde dimethylacetal 
• 173829-15-7 (2S,3R,4R,5R,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid 

Relevant articles and documents

De novo asymmetric synthesis of two 5-amino-5,6-dideoxy-D-allose derivatives

Diels-Alder cycloaddition of sorbic aldehyde derivative 9 and of sorbic acid 10 with the chiral chloro-nitroso dienophile 7 led with excellent regio- and diastereoselectivity to the chiral cycloadducts 11a and 12, respectively. Catalytic osmylation of their Bzl-derivatives 11b and 13b, followed by reductive cleavage of the N-O bonds, gave ultimately the chiral aminoallose derivatives D-5 and D-6 which are potential glycosidase inhibitors.

Synthesis of 1,6-dideoxynojirimycin, 1,6-dideoxy-D-allo-nojirimycin, and 1,6-dideoxy-D-gulo-nojirimycin via asymmetric hetero-Diels-Alder reactions

Asymmetric Diels-Alder reaction of sorbaldehyde O-methyloxime 1d with chiral chloronitroso derivative 2 of D-mannose, followed by osmylation of the primary cycloadduct, led to diol 6a with excellent enantioselectivity (ee > 99%). Catalytic hydrogenolysis