(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Base Information

Chemical Name:(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one
CAS No.:780769-10-0
Molecular Formula:C₁₆H₁₉NO₅
Molecular Weight:305.331
Hs Code.:

Synonyms:(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

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Chemical Property of (4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Chemical Property:

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Technology Process of (4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

There total 2 articles about (4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one 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:

: Allyl-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(4-methoxy-benzyloxy)-pent-2-ynyl]-amine

: 780769-10-0
(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: Pd(dba)2; 1,4-bis(diphenylphosphanyl)butane; 2-thiosalicylic acid / tetrahydrofuran / 0.67 h / 60 °C

1.2: 99 percent / aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / methanol / 12 h

2.2: 88 percent / aq. potassium carbonate / methanol / 20 °C

With toluene-4-sulfonic acid; Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol;
DOI:10.1002/anie.200460058

Reference yield:

: 218434-90-3
1-but-3-ynyloxymethyl-4-methoxy-benzene

: 780769-10-0
(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / toluene; hexane / 0.5 h / -78 °C

1.2: trimethylaluminum / toluene; hexane / 0.5 h / -78 °C

1.3: 69 percent / toluene; hexane / 12 h / -78 - 20 °C

2.1: Pd(dba)2; 1,4-bis(diphenylphosphanyl)butane; 2-thiosalicylic acid / tetrahydrofuran / 0.67 h / 60 °C

2.2: 99 percent / aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

3.1: p-toluenesulfonic acid monohydrate / methanol / 12 h

3.2: 88 percent / aq. potassium carbonate / methanol / 20 °C

With n-butyllithium; toluene-4-sulfonic acid; Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; toluene;
DOI:10.1002/anie.200460058

Reference yield: 50.0%

: 780769-10-0
(4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

: 16466-97-0,13254-27-8
1-propynylmagnesium bromide

: (4S,5S)-5-(1-Hydroxy-but-2-ynyl)-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one

Guidance literature:: (4S,5S)-5-Hydroxymethyl-4-[4-(4-methoxy-benzyloxy)-but-1-ynyl]-oxazolidin-2-one; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; Moffatt-Swern oxidation;

1-propynylmagnesium bromide; With zinc(II) chloride; In tetrahydrofuran; at -78 - 2 ℃;
DOI:10.1002/anie.200460058