(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

Base Information

Chemical Name:(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid
CAS No.:906560-62-1
Molecular Formula:C₃₉H₅₈O₅Si₂
Molecular Weight:663.058
Hs Code.:

Synonyms:(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

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Chemical Property of (2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

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Technology Process of (2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

There total 8 articles about (2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid 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: 76.0%

: 906560-61-0
(4R,5S)-3-[(2R,3S,6S,8S)-6-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxy)-2-methyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 906560-62-1
(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 24h;
DOI:10.1021/jo060314q

Reference yield:

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

: 906560-62-1
(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

Guidance literature:: Multi-step reaction with 6 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

5.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

6.1: 76 percent / LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trifluorormethanesulfonic acid; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 3.1: Swern oxidation;
DOI:10.1021/jo060314q

Reference yield:

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

: 906560-62-1
(2R,3S,6S,8S)-6-benzyloxy-3-(tert-butyldimethylsilyloxy)-8-(tert-butyldiphenylsilyloxy)-2-methylnonanoic acid

Guidance literature:: Multi-step reaction with 5 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

4.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5.1: 76 percent / LiOH*H₂O; aq. H₂O₂ / tetrahydrofuran; H₂O / 24 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 2.1: Swern oxidation;
DOI:10.1021/jo060314q