[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

Base Information

Chemical Name:[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester
CAS No.:877814-44-3
Molecular Formula:C₂₄H₃₂N₂O₈S
Molecular Weight:508.593
Hs Code.:

Synonyms:[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

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Chemical Property of [(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

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Technology Process of [(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

There total 8 articles about [(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester 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: 78.0%

: 877814-36-3
[(4R,5S)-4-(4-Methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

: 161203-15-2
N-Boc-glycine-pivalic acid mixed anhydride

: 877814-44-3
[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1h;
DOI:10.1021/ol052755m

Reference yield:

: 40630-84-0
allyl bromoacetate

: 877814-44-3
[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.9 g / Zn / tetrahydrofuran / 0.5 h / 20 - 60 °C

2: aq. HCl / dioxane / 0.17 h / 20 °C

3: 1.7 g / DMAP; Et₃N / tetrahydrofuran / 1 h / 20 °C

4: 78 percent / n-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

With hydrogenchloride; dmap; n-butyllithium; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; 1: Reformatsky reaction;
DOI:10.1021/ol052755m

Reference yield:

: 116430-17-2
[1-formyl-2-(4-methoxy-benzylsulfanyl)-ethyl]-carbamic acid tert-butyl ester

: 877814-44-3
[(4R,5S)-3-(2-tert-Butoxycarbonylamino-acetyl)-4-(4-methoxy-benzylsulfanylmethyl)-2-oxo-oxazolidin-5-yl]-acetic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.9 g / Zn / tetrahydrofuran / 0.5 h / 20 - 60 °C

2: aq. HCl / dioxane / 0.17 h / 20 °C

3: 1.7 g / DMAP; Et₃N / tetrahydrofuran / 1 h / 20 °C

4: 78 percent / n-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

With hydrogenchloride; dmap; n-butyllithium; triethylamine; zinc; In tetrahydrofuran; 1,4-dioxane; 1: Reformatsky reaction;
DOI:10.1021/ol052755m