(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

Base Information

Chemical Name:(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole
CAS No.:763122-75-4
Molecular Formula:C₄₈H₅₆N₂O₉
Molecular Weight:804.981
Hs Code.:

Synonyms:(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

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Chemical Property of (4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

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Technology Process of (4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

There total 1 articles about (4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole 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: 75.0%

: 481667-83-8
(2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbaldehyde oxime

: 151139-90-1
(4S)-2,2-dimethyl-4-prop-2'-ynyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 763122-75-4
(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

Guidance literature:: (2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbaldehyde oxime; (4S)-2,2-dimethyl-4-prop-2'-ynyl-oxazolidine-3-carboxylic acid tert-butyl ester; With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 0.5h;

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 10h;
DOI:10.1021/ol048963g

Reference yield: 90.0%

: 763122-75-4
(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

: 763122-80-1
(2''S)-5-(2''-tert-butoxycarbonylamino-3''-hydroxy-propyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 12h;
DOI:10.1021/ol048963g

Reference yield:

: 763122-75-4
(4'''S)-5-(3'''-tert-butoxycarbonyl-2''',2'''-dimethyl-oxazolidin-4'''-ylmethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

: (2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-isoxazole

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / p-TsOH*H₂O / methanol / 12 h / 20 °C

2: Jones' reagent / acetone / 3.5 h / 0 - 20 °C

3: 345 mg / diethyl ether; methanol / 0.08 h / 0 °C

With jones' reagent; toluene-4-sulfonic acid; In methanol; diethyl ether; acetone;
DOI:10.1021/ol048963g