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

Base Information

Chemical Name:(2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole
CAS No.:763122-70-9
Molecular Formula:C₄₆H₅₂N₂O₁₀
Molecular Weight:792.926
Hs Code.:

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

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Chemical Property of (2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

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Technology Process of (2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

There total 5 articles about (2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-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: 66.0%

: 71460-02-1,173306-82-6
methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate

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

: 3,4-Bis-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-furazan 2-oxide

: 763122-70-9
(2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

Guidance literature:: methyl (2S)-2-(tert-butoxycarbonylamino)pent-4-ynoate; (2S,3S,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbaldehyde oxime; With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 1h;

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

Reference yield:

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

: 763122-70-9
(2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-bromosuccinimide / dimethylformamide / 0.5 h

1.2: 68 percent / Et₃N / dimethylformamide / 10 h / 20 °C

2.1: 85 percent / p-TsOH*H₂O / methanol / 12 h / 20 °C

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

4.1: 350 mg / diethyl ether; methanol / 0.08 h / 0 °C

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

Reference yield:

: 763122-78-7
(2''S)-5-(2''-tert-butoxycarbonylamino-3''-hydroxy-propyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

: 763122-70-9
(2''S)-5-(2''-tert-butoxycarbonylamino-2''-methoxycarbonyl-ethyl)-3-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-isoxazole

Guidance literature:: Multi-step reaction with 2 steps

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

2: 350 mg / diethyl ether; methanol / 0.08 h / 0 °C

With jones' reagent; In methanol; diethyl ether; acetone;
DOI:10.1021/ol048963g