[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

Base Information

Chemical Name:[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane
CAS No.:896110-46-6
Molecular Formula:C₅₃H₆₆O₅Si₂
Molecular Weight:839.275
Hs Code.:

Synonyms:[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

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Chemical Property of [(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

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Technology Process of [(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

There total 15 articles about [(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane 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: 96.0%

: 896110-45-5
11-benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxymethyl)-undec-2-en-7-yn-6-ol

: 107-30-2
chloromethyl methyl ether

: 896110-46-6
[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 8.5h;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: 896110-40-0
(E)-(R)-5-(tert-butyldiphenylsilyloxy)pent-3-ene-1,2-diol

: 896110-46-6
[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

Guidance literature:: Multi-step reaction with 10 steps

1.1: 82 percent / imidazole / tetrahydrofuran / 7 h / -15 °C

2.1: 92 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

3.1: tert-butyldimethylsilyl chloride / tetrahydrofuran

3.2: potassium hexamethyldisilazide / tetrahydrofuran / -78 - 20 °C

3.3: 100 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

4.1: 73 percent / K₂CO₃ / dimethylformamide / 1.5 h / 20 °C

5.1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / -78 - 20 °C

6.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

8.1: 95 percent / MnO₂ / CH₂Cl₂ / 19 h

9.1: (R)-CBS; BH₃ / tetrahydrofuran / 1.25 h / -78 - -40 °C

10.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; n-butyllithium; oxalyl dichloride; borane; diisobutylaluminium hydride; potassium carbonate; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Swern oxidation;
DOI:10.1016/j.tet.2005.11.096

Reference yield:

: 896110-69-3
(E)-(R)-1,5-Bis-(tert-butyl-diphenyl-silanyloxy)-pent-3-en-2-ol

: 896110-46-6
[(E)-(4S,6R)-11-benzyloxy-4-(tert-butyldiphenylsilyloxymethyl)-(6-methoxymethoxy)undec-2-en-7-ynyl]oxy-tert-butyldiphenylsilane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: tert-butyldimethylsilyl chloride / tetrahydrofuran

2.2: potassium hexamethyldisilazide / tetrahydrofuran / -78 - 20 °C

2.3: 100 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 0 °C

3.1: 73 percent / K₂CO₃ / dimethylformamide / 1.5 h / 20 °C

4.1: 95 percent / DIBAL-H / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: 87 percent / tetrahydrofuran; hexane / 1 h / -78 - -40 °C

7.1: 95 percent / MnO₂ / CH₂Cl₂ / 19 h

8.1: (R)-CBS; BH₃ / tetrahydrofuran / 1.25 h / -78 - -40 °C

9.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With pyridine; dmap; manganese(IV) oxide; n-butyllithium; oxalyl dichloride; borane; diisobutylaluminium hydride; potassium carbonate; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation;
DOI:10.1016/j.tet.2005.11.096