(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

Base Information

Chemical Name:(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide
CAS No.:750646-38-9
Molecular Formula:C₃₂H₅₁NO₆Si
Molecular Weight:573.846
Hs Code.:

Synonyms:(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

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Chemical Property of (2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

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Technology Process of (2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

There total 6 articles about (2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide 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: 84.0%

: 750646-37-8
(4R,5S)-3-[(2R,3S,6S,7S,8S)-9-(tert-butyldiphenylsilyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 750646-38-9
(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 20 ℃; for 0.5h;

(4R,5S)-3-[(2R,3S,6S,7S,8S)-9-(tert-butyldiphenylsilyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoyl]-4-methyl-5-phenyl-oxazolidin-2-one; In tetrahydrofuran; toluene; at -20 - 0 ℃; for 15h;
DOI:10.1002/chem.200305543

Reference yield:

: 750646-33-4
tert-Butyl-((2S,3S,4S)-3-methoxymethoxy-2,4-dimethyl-hept-6-enyloxy)-diphenyl-silane

: 750646-38-9
(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-BBN / tetrahydrofuran / 15 h / 20 °C

1.2: 86 percent / aq. NaOH; H₂O₂ / 24 h / 20 °C

2.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

3.1: Bu₂BOTf; (i-Pr)2NEt / CH₂Cl₂ / 0.75 h / 0 °C

3.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

3.3: 486 mg / H₂O₂ / CH₂Cl₂ / pH 7

4.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

4.2: 84 percent / toluene; tetrahydrofuran / 15 h / -20 - 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.200305543

Reference yield:

: (4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-methoxymethoxy-4,6-dimethyl-heptanal

: 750646-38-9
(2R,3S,6S,7S,8S)-9-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-7-methoxymethoxy-2,6,8-trimethyl-nonanoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 2 steps

1.1: Bu₂BOTf; (i-Pr)2NEt / CH₂Cl₂ / 0.75 h / 0 °C

1.2: CH₂Cl₂ / 1.5 h / -78 - 20 °C

1.3: 486 mg / H₂O₂ / CH₂Cl₂ / pH 7

2.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

2.2: 84 percent / toluene; tetrahydrofuran / 15 h / -20 - 0 °C

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/chem.200305543