(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:906560-60-9
Molecular Formula:C₄₃H₅₃NO₆Si
Molecular Weight:707.982
Hs Code.:

Synonyms:(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 5 articles about (4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-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:

: 906560-57-4
(4S,6S)-6-(tert-butyldiphenylsilyloxy)-hept-1-en-4-ol

: 906560-60-9
(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / CF₃SO₃H / CH₂Cl₂ / 3 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 18 h / 20 °C

2.2: 77 percent / aq. NaOH; aq. H₂O / tetrahydrofuran; methanol / 1 h / 50 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.2: 1.19 g / CH₂Cl₂ / 18 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1021/jo060314q

Reference yield:

: 906560-58-5
(4S,6S)-4-benzyloxy-6-(tert-butyldiphenylsilyloxy)-hept-1-ene

: 906560-60-9
(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9-BBN / tetrahydrofuran / 18 h / 20 °C

1.2: 77 percent / aq. NaOH; aq. H₂O / tetrahydrofuran; methanol / 1 h / 50 °C

2.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

3.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

3.2: 1.19 g / CH₂Cl₂ / 18 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;
DOI:10.1021/jo060314q

Reference yield:

: 906560-59-6
(4S,6S)-4-benzyloxy-6-(tert-butyldiphenylsilyloxy)-heptan-1-ol

: 906560-60-9
(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1 h / 0 °C

2.2: 1.19 g / CH₂Cl₂ / 18 h / 0 °C

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo060314q