(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:1141741-71-0
Molecular Formula:C₂₆H₄₃NO₅
Molecular Weight:449.631
Hs Code.:

Synonyms:(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of (S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

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Technology Process of (S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 8 articles about (S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate 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:

: C₃₀H₅₁NO₇SSi

: 1141741-71-0
(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C

1.2: 1 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.25 h / -20 °C / Molecular sieve

3.2: 30 h / -20 °C / Molecular sieve

4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 0 °C / Darkness

5.1: zinc / methanol / 2 h / Reflux

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

6.2: 0 - 20 °C

7.1: borane-THF / tetrahydrofuran / 2 h / 0 - 20 °C

7.2: 20 °C / pH 9.2 / aq. phosphate buffer

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

8.2: -78 - 20 °C

9.1: diethyl ether / 1.5 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil; 7.1: Hydroboration reaction / 8.1: Swern oxidation / 8.2: Swern oxidation;
DOI:10.1002/psc.1433

Reference yield:

: 1141741-67-4
(S)-tert-butyl 4-((S)-3-((2S,3S)-3-(hydroxymethyl)oxiran-2-yl)-2-methylpropyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1141741-71-0
(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 0 °C / Darkness

2.1: zinc / methanol / 2 h / Reflux

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

3.2: 0 - 20 °C

4.1: borane-THF / tetrahydrofuran / 2 h / 0 - 20 °C

4.2: 20 °C / pH 9.2 / aq. phosphate buffer

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

5.2: -78 - 20 °C

6.1: diethyl ether / 1.5 h / 0 - 20 °C

With 1H-imidazole; borane-THF; oxalyl dichloride; iodine; sodium hydride; dimethyl sulfoxide; triphenylphosphine; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil; 4.1: Hydroboration reaction / 5.1: Swern oxidation / 5.2: Swern oxidation;
DOI:10.1002/psc.1433

Reference yield:

: 1141741-64-1
(S)-tert-butyl 4-((R,E)-6-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)hex-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1141741-71-0
(S)-tert-butyl 4-((2S,4S)-4-benzyloxy-6-hydroxy-2-methyloctyl)-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: dmap; triethylamine / dichloromethane / 0 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 3 h / 0 - 20 °C

2.2: 1 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.25 h / -20 °C / Molecular sieve

4.2: 30 h / -20 °C / Molecular sieve

5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 0 °C / Darkness

6.1: zinc / methanol / 2 h / Reflux

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C

7.2: 0 - 20 °C

8.1: borane-THF / tetrahydrofuran / 2 h / 0 - 20 °C

8.2: 20 °C / pH 9.2 / aq. phosphate buffer

9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -78 °C

9.2: -78 - 20 °C

10.1: diethyl ether / 1.5 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; iodine; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; mineral oil; 8.1: Hydroboration reaction / 9.1: Swern oxidation / 9.2: Swern oxidation;
DOI:10.1002/psc.1433