(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine
• CAS No.: 1415608-17-1
• Molecular Formula: C₄₀H₄₁NO₅
• Molecular Weight: 615.769
• Mol file: 1415608-17-1.mol

Synonyms:(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine

Chemical Property of (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine

There total 3 articles about (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine 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: 81.0%

benzyl 2-amino-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranoside hydrochloride + iodobenzene (591-50-4) → (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine (1415608-17-1)

Guidance literature:

With copper(l) iodide; 2-acetylcyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1016/j.tetlet.2012.10.069

Reference yield: 65.0%

benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (62098-37-7) + phenylboronic acid (98-80-6) → (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine (1415608-17-1)

Guidance literature:

phenylboronic acid; With copper diacetate; In dichloromethane; acetonitrile; at 20 ℃; for 0.166667h; Molecular sieve;

benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside; In dichloromethane; acetonitrile; at 65 ℃; for 24h; Reagent/catalyst; Solvent; Molecular sieve;

DOI:10.1080/07328303.2013.816851

Reference yield:

D-glucosamine hydrochloride (14131-63-6) → (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine (1415608-17-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methoxy-benzaldehyde; sodium hydride / Acidic conditions

2: copper(l) iodide; caesium carbonate; 2-acetylcyclohexanone / N,N-dimethyl-formamide / 130 °C / Schlenk technique; Inert atmosphere; Sealed tube

With copper(l) iodide; 2-acetylcyclohexanone; sodium hydride; caesium carbonate; 4-methoxy-benzaldehyde; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2012.10.069

upstream raw materials:

D-glucosamine hydrochloride

iodobenzene

benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

phenylboronic acid

Downstream raw materials:

(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-triol