(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

Base Information

Chemical Name:(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne
CAS No.:676254-81-2
Molecular Formula:C₄₀H₆₆O₆Si₂
Molecular Weight:699.131
Hs Code.:

Synonyms:(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

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Chemical Property of (3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

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Technology Process of (3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

There total 26 articles about (3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne 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: 89.0%

: 676254-80-1
C₄₃H₇₄O₆Si₃

: 676254-81-2
(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

Guidance literature:: With potassium carbonate; In methanol;
DOI:10.1016/j.tetlet.2003.12.067

Reference yield:

: 455948-89-7
tert-butyl-[(2S,3S,4S)-3-methoxymethoxy-2,4-dimethyl-hept-6-enyloxy]-dimethylsilane

: 676254-81-2
(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 83 percent / aq. NaOH; H₂O₂ / 24 h / 20 °C

2.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

3.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

3.2: CH₂Cl₂ / 3 h / -78 - 20 °C

3.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

4.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

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

5.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

6.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

7.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

7.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

7.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

8.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

9.1: imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Swern oxidation / 3.1: Evans aldol reaction;
DOI:10.1002/chem.200305543

Reference yield:

: 750646-35-6
(4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-4,6-dimethyl-heptanal

: 676254-81-2
(3R,4R,5S,8S,9S,10S)-11-(tert-butyldimethylsilyloxy)-3-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,8,10-trimethyl-undec-1-yne

Guidance literature:: Multi-step reaction with 7 steps

1.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

1.2: CH₂Cl₂ / 3 h / -78 - 20 °C

1.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

2.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

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

3.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

4.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

5.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

5.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

6.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

7.1: imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Evans aldol reaction;
DOI:10.1002/chem.200305543