135395-47-0

Basic information

• Product Name: (3R,4R,5S)-2-Methyl-piperidine-3,4,5-triol
• CAS NO: 135395-47-0
• Molecular Weight: 147.174
• Mol File: 135395-47-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (3R,4R,5S)-2-Methyl-piperidine-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5S)-2-Methyl-piperidine-3,4,5-triol(135395-47-0)
• EPA Substance Registry System: (3R,4R,5S)-2-Methyl-piperidine-3,4,5-triol(135395-47-0)

Safety Data

• Hazardous Substances Data: 135395-47-0(Hazardous Substances Data)

Upstream product

• 17682-70-1 2,3:4,6-bis-O-isopropylidene-L-sorbose 
• 144848-63-5 (3aR,5S,6R,6aS)-5-Azidomethyl-3a-fluoromethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 144848-61-3 (3aR,5S,6R,6aS)-3a-Fluoromethyl-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 197567-75-2 (3aS,4R,7R,7aR)-4-Dimethoxymethyl-7-methyl-2,2-dioxo-tetrahydro-1,3,5-trioxa-2λ⁶-thia-6-aza-indene-6-carboxylic acid benzyl ester 
• 173933-53-4 (3R,4S,5S,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 173602-42-1 (3R,4R,5S,6R)-6-Dimethoxymethyl-3-methyl-4,5-bis-trifluoromethanesulfonyloxy-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 173829-12-4 (3R,4R,5R,6R)-6-Dimethoxymethyl-4,5-dihydroxy-3-methyl-[1,2]oxazinane-2-carboxylic acid benzyl ester 
• 314252-41-0 Acetic acid (2R,3S,4S,5R)-3,5-diacetoxy-2-methyl-6-oxo-piperidin-4-yl ester 
• 207295-99-6 (3aR,6S,6aR)-dihydro-6-(azidomethyl)-2,2-dimethylfuro-[3,4-d]-1,3-dioxol-4(3aH)-one 
• 152006-17-2 2,3-O-isopropylidene-L-lyxono-1,4-lactone 
• 324759-96-8 (3aS,4R,7S,7aR)-hexahydro-2,2,4-trimethyl-1,3-dioxolo-[4,5c]pyridine-7-ol 
• 692776-34-4 6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide 
• 173829-16-8 (2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-methyl-piperidine-2-sulfonic acid 
• 136616-69-8 Phosphoric acid mono-((3R,4R,5S)-6-azido-3,4,5-trihydroxy-2-oxo-hexyl) ester 

Relevant articles and documents

A general approach to the synthesis of dideoxy and trideoxyiminoalditols from β-D-glycosides

Imino sugars (also called azasugars), a class of compounds of which the 1,5-dideoxy and 1,5,6-trideoxyiminoalditols are members, are important glycosidase inhibitors with very high potential as drugs. Their potential therapeutic applications range from the treatment of diabetes to cancer and AIDS. We present here a general method for the preparation of such compounds with the D-gluco and D-galacto configurations starting from β-D-glycosides. The procedure is especially appealing because of its high stereoselectivity and straightforwardness. The key steps are the selective oxidation of the glycosides to hexulosonic acids and reduction of the oxime derivatives to lactams, which are further reduced to the target compounds. The C-6 position can be deoxygenated during the reduction if it bears an acetoxy group. Trideoxy imino sugars are then produced. Deacetylation prior to oxime reduction gives dideoxy compounds. (C) 2000 Elsevier Science Ltd.

A General Synthesis of Iminosugars

1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyl azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-β-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

Fluorinated 1,5-Dideoxy-1,5-iminoalditols: Synthesis of 1,5,6-Trideoxy-6-fluoro-1,5-imino-D-glucitol (1,6-Dideoxy-6-fluoronojirimycin) and 1,4,5-Trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-Trideoxy-2-fluoro-1,5-imino-L-ribitol)

An efficient synthesis of 1,5,6-trideoxy-6-fluoro-1,5-imino-D-glucitol 13 from inexpensive L-sorbose by way of reductive amination of 12 is described.Synthesis of 1,4,5-trideoxy-4-fluoro-1,5-imino-D-ribitol (1,2,5-trideoxy-2-fluoro-1,5-imino-L-ribitol) 19