(2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol
• CAS No.: 72458-46-9
• Molecular Formula: C13H19NO4
• Molecular Weight: 253.298
• Mol file: 72458-46-9.mol

Synonyms:N-benzyl-1,5-dideoxy-1,5-imino-D-glucitol;(2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol;N-(1-phenylmethyl)-1,5-dideoxy-1,5-imino-D-glucitol;N-benzyldeoxynojirimycin;

Chemical Property of (2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol

Chemical Property:

• PSA: 84.16000
• LogP: -1.11630

Purity/Quality:

(2R,3R,4R,5S)-1-Benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol

There total 15 articles about (2R,3R,4R,5S)-1-benzyl-2-(hydroxymethyl)piperidine-3,4,5-triol 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: 87.0%

(3aS,6R,7R,7aS)-5-Benzyl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol (214342-01-5) → N-benzyl-1-deoxynojirimycin (72458-46-9)

Guidance literature:

With trifluoroacetic acid; In methanol;

DOI:10.1016/S0040-4039(98)01536-6

Reference yield: 50.0%

1,5-dideoxy-1,5-imino-D-glucitol (19130-96-2) + benzyl bromide (100-39-0) → N-benzyl-1-deoxynojirimycin (72458-46-9)

Guidance literature:

In water; acetonitrile;

DOI:10.1016/S0960-894X(99)00175-4

Reference yield:

N-Benzhydryl-1-deoxynojirimycin (132198-14-2) → N-benzyl-1-deoxynojirimycin (72458-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / H₂ / Pd/C / methanol

2: 50 percent / acetonitrile; H₂O

With hydrogen; palladium on activated charcoal; In methanol; water; acetonitrile;

DOI:10.1016/S0960-894X(99)00175-4

upstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

benzyl bromide

(3aS,6R,7R,7aS)-5-Benzyl-6-hydroxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol

N-Benzhydryl-1-deoxynojirimycin

Downstream raw materials:

N-benzyl-3-O-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-2-O-(trifluoro-methyl)sulfonyl-D-mannitol

N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-2,3-di-O-(methylsulfonyl)-D-glucitol

2-azido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

2-acetamido-N-benzyl-3-O-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol

Refernces

• 1、 -. "Use of n-substituted-1,5-dideoxy-1,5-imino-d-glucitol compounds for treating hepatitis virus infections". . . Retrieved 2008/06/13.
• 2、 -. "USE OF N-SUBSTITUTED-1,5-DIDEOXY-1,5-IMINO-D-GLUCITOL COMPOUNDS IN COMBINATION THERAPY FOR TREATING HEPATITIS VIRUS INFECTIONS". . . Retrieved 2008/06/13.