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

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-p-tolyltetrahydro-2H-pyran-3-amine
CAS No.:1415608-19-3
Molecular Formula:C₄₁H₄₃NO₅
Molecular Weight:629.796
Hs Code.:

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

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

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

There total 3 articles about (2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-p-tolyltetrahydro-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: 72.0%

: benzyl 2-amino-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranoside hydrochloride

: 624-31-7
4-tolyl iodide

: 1415608-19-3
(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-p-tolyltetrahydro-2H-pyran-3-amine

Guidance literature:: With copper(l) iodide; 2-acetylcyclohexanone; caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; Schlenk technique; Inert atmosphere; Sealed tube;
DOI:10.1016/j.tetlet.2012.10.069

Reference yield:

: 62098-37-7
benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

: 5720-05-8
4-methylphenylboronic acid

: 1415608-19-3
(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-p-tolyltetrahydro-2H-pyran-3-amine

Guidance literature:: 4-methylphenylboronic 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; Molecular sieve;
DOI:10.1080/07328303.2013.816851

Reference yield:

: 14131-63-6
D-glucosamine hydrochloride

: 1415608-19-3
(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-p-tolyltetrahydro-2H-pyran-3-amine

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