(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
CAS No.:115384-70-8
Molecular Formula:C₃₀H₅₂N₂O₆Si
Molecular Weight:564.838
Hs Code.:

(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 6 articles about (4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

: 115384-68-4
[(5S,6S)-5-tert-Butoxycarbonylamino-8-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-octyl]-carbamic acid benzyl ester

: 77-76-9
2,2-dimethoxy-propane

: 115384-70-8
(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: With camphor-10-sulfonic acid; In acetone; at 60 ℃; for 3h; Yield given;
DOI:10.1021/jo00251a051

Reference yield:

: 82689-16-5
benzyl {(5S)-5-[(tert-butoxycarbonyl)amino]-6-oxohexyl}carbamate

: 115384-70-8
(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

2: BF₃*Et₂O, i-Bu₂AlH / CH₂Cl₂ / 1 h / -78 °C

3: 1.) MCPBA, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 14 h, 2.) Et₂O, RT, 2.5 h

4: imidazole / dimethylformamide / 2 h / 0 °C

5: CSA / acetone / 3 h / 60 °C

With 1H-imidazole; lithium aluminium tetrahydride; 18-crown-6 ether; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium hexamethylsilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00251a051

Reference yield:

: 82689-20-1,252940-35-5
N⁶-benzyloxycarbonyl-N²-tert-butoxycarbonyl-L-lysinol

: 115384-70-8
(4S,5S)-4-(4-Benzyloxycarbonylamino-butyl)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: SO₃, pyridine / dimethylsulfoxide / 0.17 h / Ambient temperature

2: KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 0.5 h / -78 °C

3: BF₃*Et₂O, i-Bu₂AlH / CH₂Cl₂ / 1 h / -78 °C

4: 1.) MCPBA, 2.) LiAlH₄ / 1.) CH₂Cl₂, 0 deg C, 14 h, 2.) Et₂O, RT, 2.5 h

5: imidazole / dimethylformamide / 2 h / 0 °C

6: CSA / acetone / 3 h / 60 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; 18-crown-6 ether; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sulfur trioxide; potassium hexamethylsilazane; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00251a051