(2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine

Base Information

• Chemical Name: (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine
• CAS No.: 150085-57-7
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• Mol file: 150085-57-7.mol

Synonyms:(2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine

Chemical Property of (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine

There total 10 articles about (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

(3S,4S,5S)-5-Azidomethyl-2-fluoromethyl-tetrahydro-furan-2,3,4-triol → (3R,4R,5S)-2-Methyl-piperidine-3,4,5-triol (73861-92-4,99212-30-3,134735-66-3,134735-70-9,135395-45-8,135395-47-0,135395-58-3,135395-60-7,147006-77-7,150085-57-7,528593-83-1)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol;

Reference yield: 52.0%

(3S,4S,5S,6S,2'S,4'S,5'R)-2-benzyloxycarbonyl-4,5-dihydroxy-6-(3,4-dimethyl-5-phenyloxazolidin-2-yl)-3-methyl-3,4,5,6-tetrahydro-1,2-oxazine (150085-16-8) → ephedrine hydrochloride (50-98-6) + (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine (150085-57-7,449729-69-5,528593-83-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 25h; under 1500.1 Torr; Ambient temperature;

DOI:10.1016/S0040-4020(01)86312-2

Reference yield:

(E,E,2S,4S,5R)-3,4-dimethyl-2-(penta-1,3-dien-1-yl)-5-phenyloxazolidine (150085-14-6) → (2S,3S,4R,5R)-2-methyl-3,4,5-trihydroxypiperidine (150085-57-7,449729-69-5,528593-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) 4 Angstroem molecular sieves, 2) tetrabutylammonium periodate / 1) dichloromethane, room temperature, 24 h, 2) dichloromethane, -65 deg C to room temperature, 2 h

2: 49 percent / barium chlorate monohydrate / osmium(VIII) oxide / H₂O; 2-methyl-propan-2-ol / 28 h / 20 °C

3: 64 percent / H₂ / 5percent palladium on carbon / ethanol / 25 h / 1500.1 Torr / Ambient temperature

With barium chlorate monohydrate; 4 A molecular sieve; hydrogen; tetrabutylammonium periodite; palladium on activated charcoal; osmium(VIII) oxide; In ethanol; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)86312-2

upstream raw materials:

(3aR,5S,6R,6aS)-3a-Fluoromethyl-5-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

(3aR,5S,6R,6aS)-5-Azidomethyl-3a-fluoromethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

Toluene-4-sulfonic acid (3aR,5S,6R,6aS)-3a-fluoromethyl-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Trifluoro-methanesulfonic acid (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-8a-ylmethyl ester

Refernces

• 1、 Di, Jie,Rajanikanth, Bandaru,Szarek, Walter A.. "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)". . p. 2151 - 2154. Retrieved 2007/10/02.