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

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-triol
CAS No.:121409-03-8
Molecular Formula:C₁₂H₁₇NO₅
Molecular Weight:255.271
Hs Code.:

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

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

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

There total 6 articles about (2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-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: 76.0%

: 1415608-17-1
(2R,3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-N-phenyltetrahydro-2H-pyran-3-amine

: 121409-03-8
(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-triol

Guidance literature:: With palladium 10% on activated carbon; hydrogen; trichloroacetic acid; In methanol; ethyl acetate; at 40 ℃; for 40h; Schlenk technique; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.10.069

Reference yield:

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

: 591-50-4
iodobenzene

: 121409-03-8
(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

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

2: palladium 10% on activated carbon; trichloroacetic acid; hydrogen / methanol; ethyl acetate / 40 h / 40 °C / Schlenk technique; Inert atmosphere

With copper(l) iodide; 2-acetylcyclohexanone; palladium 10% on activated carbon; hydrogen; caesium carbonate; trichloroacetic acid; In methanol; ethyl acetate; N,N-dimethyl-formamide;
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

: 98-80-6
phenylboronic acid

: 121409-03-8
(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-(phenylamino)tetrahydro-2H-pyran-2,4,5-triol

Guidance literature:: Multi-step reaction with 2 steps

1.1: copper diacetate / dichloromethane; acetonitrile / 0.17 h / 20 °C / Molecular sieve

1.2: 24 h / 65 °C / Molecular sieve

2.1: hydrogen; palladium 10% on activated carbon; trichloroacetic acid / methanol; ethyl acetate / 40 h / 40 °C

With palladium 10% on activated carbon; hydrogen; copper diacetate; trichloroacetic acid; In methanol; dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1080/07328303.2013.816851