1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol

Base Information

• Chemical Name: 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol
• CAS No.: 410077-69-9
• Molecular Formula: C₂₂H₃₀O₂Si
• Molecular Weight: 354.565
• Mol file: 410077-69-9.mol

Synonyms:1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol

Chemical Property of 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol

There total 1 articles about 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol 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: 83.0%

vinyl magnesium bromide (1826-67-1) + (S)-1-(tert-butyldiphenylsilyloxy)methyl-1-methyloxirane (184091-30-3) → 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol (410077-69-9)

Guidance literature:

vinyl magnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -40 ℃; for 1h;

(S)-1-(tert-butyldiphenylsilyloxy)methyl-1-methyloxirane; In tetrahydrofuran; at -45 - 0 ℃; Further stages.;

DOI:10.1021/ol017273z

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + 1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol (410077-69-9) → carbonic acid tert-butyl ester 1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-but-3-enyl ester (410077-35-9)

Guidance literature:

1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

di-tert-butyl dicarbonate; In tetrahydrofuran; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/ol017273z

Reference yield:

1-(tert-butyl-diphenyl-silanyloxy)-2-methyl-pent-4-en-2-ol (410077-69-9) → C63H110O14Si3

Guidance literature:

Multi-step reaction with 17 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

1.2: 99 percent / tetrahydrofuran / 1 h / 20 °C

2.1: IBr / diethyl ether; CH₂Cl₂ / 3.5 h / -100 - -78 °C

3.1: 91 percent / K₂CO₃ / methanol / 2.5 h / 20 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 - 0 °C

4.2: 88 percent / n-BuLi / tetrahydrofuran; pentane; hexane / 3 h / -45 - 0 °C

5.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

6.1: NaH / tetrahydrofuran / 1 h / 0 °C

6.2: 73 percent / 2,4,6-triisopropylbenzenesulfonyl imidazole / tetrahydrofuran / 1.5 h / 0 °C

7.1: t-BuLi / diethyl ether; pentane / 0.83 h / -78 - -45 °C

7.2: diethyl ether; pentane / 4 h / -45 - -20 °C

7.3: 58 percent / HMPA; n-BuLi / hexane; diethyl ether; tetrahydrofuran / 15 h / -20 °C

8.1: Hg(ClO₄)2*4H₂O / acetonitrile; H₂O; CH₂Cl₂ / 0.17 h / 0 °C

8.2: 83 percent / HClO₄ / acetonitrile; H₂O; CH₂Cl₂ / 0.08 h

9.1: 90 percent / pyridine; 4-DMAP / CH₂Cl₂ / 13 h

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

11.1: 98 percent / 2-methylcyclohexadiene; calcium carbonate / Pd(OH)2/C / ethanol / 5.5 h / 70 °C

12.1: 99 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.33 h

13.1: 100 percent / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / ethyl-1-propenyl ether / H₂O; tetrahydrofuran; 2-methyl-propan-2-ol / 6 h / 20 °C

14.1: 97 percent / Et₃N / CH₂Cl₂; tetrahydrofuran / 0.5 h

15.1: 91 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 0 °C

16.1: 89 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h

17.1: dicyclohexylboron chloride; triethylamine / pentane / -78 - 0 °C

17.2: pentane / 6.5 h / -78 °C

17.3: 64 percent / H₂O₂ / pentane; methanol / 1 h / 0 °C / pH 7

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; mercury(II) perchlorate; 2-methyl-but-2-ene; 2-methylcyclohexa-1,3-diene; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; iodine(I) bromide; sodium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; palladium dihydroxide; ethyl-1-propenyl ether; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; pentane; 12.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation;

DOI:10.1021/ol017273z

upstream raw materials:

vinyl magnesium bromide

(S)-1-(tert-butyldiphenylsilyloxy)methyl-1-methyloxirane

Downstream raw materials:

carbonic acid tert-butyl ester 1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-but-3-enyl ester

(2S,4S,6R,8S,10S)-2-[(R)-4-(4-Methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-4-methyl-8-[2-(naphthalen-2-ylmethoxy)-ethyl]-1,7-dioxa-spiro[5.5]undecane-4,10-diol

Acetic acid (2S,4S,6R,8S,10S)-10-hydroxy-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-2-[2-(naphthalen-2-ylmethoxy)-ethyl]-1,7-dioxa-spiro[5.5]undec-4-yl ester

Acetic acid (2S,4S,6R,8S,10S)-8-[(R)-4-(4-methoxy-benzyloxy)-3-methyl-2-methylene-butyl]-10-methyl-2-[2-(naphthalen-2-ylmethoxy)-ethyl]-10-triethylsilanyloxy-1,7-dioxa-spiro[5.5]undec-4-yl ester