(2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal

Base Information

• Chemical Name: (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal
• CAS No.: 382138-91-2
• Molecular Formula: C₄₄H₆₈O₅Si₂
• Molecular Weight: 733.192
• Mol file: 382138-91-2.mol

Synonyms:(2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal

Chemical Property of (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal

There total 20 articles about (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal 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: 95.0%

(2S,3S,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decan-1-ol (382139-13-1) → (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal (382138-91-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1002/1521-3773(20011001)40:19<3632::AID-ANIE3632>3.0.CO;2-5

Reference yield:

(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one (182193-69-7) → (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal (382138-91-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; tin(II) triflate / CH₂Cl₂ / 2 h / -78 °C

1.2: 2.30 g / CH₂Cl₂ / 5 h / -78 °C

2.1: 82 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / -25 - 0 °C

3.1: 85 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 0 °C

4.1: 99 percent / imidazole / dimethylformamide / 3 h / 50 °C

5.1: 87 percent / Dibal-H / CH₂Cl₂; toluene / 1 h / 0 °C

6.1: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

With 1H-imidazole; tin(II) trifluoromethanesulfonate; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Swern oxidation;

DOI:10.1021/ja020091v

Reference yield:

(2S,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methyl-hexanal (253143-33-8) → (2R,3R,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decanal (382138-91-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; tin(II) triflate / CH₂Cl₂ / 2 h / -78 °C

1.2: 2.30 g / CH₂Cl₂ / 5 h / -78 °C

2.1: 82 percent / Me₄NBH(OAc)3; AcOH / acetonitrile / -25 - 0 °C

3.1: 85 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 0 °C

4.1: 99 percent / imidazole / dimethylformamide / 3 h / 50 °C

5.1: 87 percent / Dibal-H / CH₂Cl₂; toluene / 1 h / 0 °C

6.1: 95 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - -20 °C

With 1H-imidazole; tin(II) trifluoromethanesulfonate; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Swern oxidation;

DOI:10.1021/ja020091v

upstream raw materials:

(2S,3S,4S,5S,6S,8S)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,4,6-trimethyl-5-triethylsilanyloxy-decan-1-ol

O-(4-methoxybenzyl)-trichloroacetimidate

(2S)-2-ethyl-4-penten-1-ol

(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

Downstream raw materials:

(2S,3S,4S,5S,6R,9S,11S)-9-Ethyl-2-((2S,3S)-2-hydroxy-3-methyl-hept-6-ynyl)-4-(4-methoxy-benzyloxy)-3,5,11-trimethyl-1-oxa-7-aza-spiro[5.5]undecan-8-one

(2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonane-1,5-diol

(2S,4S,6S,7S,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-7-(4-methoxy-benzyloxy)-4,6-dimethyl-5-oxo-nonanoic acid amide

(2S,4S,5S,6R,7R,8S)-8-[(4S,6S)-2,2-Dimethyl-6-((S)-1-methyl-pent-4-ynyl)-[1,3]dioxan-4-yl]-2-ethyl-5-hydroxy-7-(4-methoxy-benzyloxy)-4,6-dimethyl-nonanoic acid amide