(2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene

Base Information

• Chemical Name: (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene
• CAS No.: 912457-45-5
• Molecular Formula: C₃₅H₅₀O₄Si
• Molecular Weight: 562.865
• Mol file: 912457-45-5.mol

Synonyms:(2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene

Chemical Property of (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene

There total 18 articles about (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene 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: 99.0%

(2R)-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-en-2-ol (912457-44-4) + allyl bromide (106-95-6) → (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene (912457-45-5)

Guidance literature:

With 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol061439k

Reference yield:

6-(4-methoxyphenoxy)hex-1-yne (912457-49-9) → (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene (912457-45-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 95 percent / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 97 percent / Ph₃P; phenol / benzene / 12 h / 20 °C

3.1: K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 0 °C

3.2: pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

4.1: 93 percent / HCO₂H; PPh₃; triethylamine / Pd₂(dba)3*HCl / tetrahydrofuran / 20 °C

5.1: 61 percent / t-BuOK / tetrahydrofuran / 0 °C

6.1: 89 percent / iPrMgCl / tetrahydrofuran / 1 h / -20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 84 percent / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: Cs₂CO₃ / propan-2-ol / 0.08 h / 0 °C

8.2: 82 percent / propan-2-ol / 3 h / 20 °C

9.1: 58 percent / K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 5 h / 0 °C

10.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

11.1: 83 percent / HCO₂H; triethylamine; PPh₃ / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 20 °C

12.1: 92 percent / H₂ / Pd/C / methanol / 12 h / 760 Torr

13.1: 94 percent / imidazole / dimethylformamide / 12 h / 50 °C

14.1: 96 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h / 0 °C

15.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

16.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

16.2: CuCN / pentane; diethyl ether / -78 - 0 °C

16.3: 78 percent / pentane; diethyl ether / -78 - 0 °C

17.1: 99 percent / KH; 18-crown-6; Bu₄NI / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; formic acid; ammonium cerium(IV) nitrate; 18-crown-6 ether; potassium tert-butylate; hydrogen; tert.-butyl lithium; isopropylmagnesium chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); phenol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; methanesulfonamide; Pd₂(dba)3*HCl; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; tert-butyl alcohol; pentane; benzene; 7.2: Horner-Wadsworth-Emmons reaction / 8.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ol061439k

Reference yield:

ethyl 7-(4-methoxyphenoxy)hepta-2,4-dienoate (912457-35-3) → (2R)-2-allyloxy-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-ene (912457-45-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 0 °C

1.2: pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

2.1: 93 percent / HCO₂H; PPh₃; triethylamine / Pd₂(dba)3*HCl / tetrahydrofuran / 20 °C

3.1: 61 percent / t-BuOK / tetrahydrofuran / 0 °C

4.1: 89 percent / iPrMgCl / tetrahydrofuran / 1 h / -20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: 84 percent / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: Cs₂CO₃ / propan-2-ol / 0.08 h / 0 °C

6.2: 82 percent / propan-2-ol / 3 h / 20 °C

7.1: 58 percent / K₃[Fe(CN)6]; OsO₄; K₂CO₃ / MeSO₂NH₂; (DHQD)2-PHAL / 2-methyl-propan-2-ol; H₂O / 5 h / 0 °C

8.1: 98 percent / pyridine; DMAP / CH₂Cl₂ / 2 h / -78 - 0 °C

9.1: 83 percent / HCO₂H; triethylamine; PPh₃ / Pd₂(dba)3*CHCl₃ / tetrahydrofuran / 20 °C

10.1: 92 percent / H₂ / Pd/C / methanol / 12 h / 760 Torr

11.1: 94 percent / imidazole / dimethylformamide / 12 h / 50 °C

12.1: 96 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h / 0 °C

13.1: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

14.1: t-BuLi / pentane; diethyl ether / 1 h / -78 °C

14.2: CuCN / pentane; diethyl ether / -78 - 0 °C

14.3: 78 percent / pentane; diethyl ether / -78 - 0 °C

15.1: 99 percent / KH; 18-crown-6; Bu₄NI / tetrahydrofuran / 3 h / 20 °C

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; n-butyllithium; formic acid; ammonium cerium(IV) nitrate; 18-crown-6 ether; potassium tert-butylate; hydrogen; tert.-butyl lithium; isopropylmagnesium chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; methanesulfonamide; Pd₂(dba)3*HCl; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; tert-butyl alcohol; pentane; 5.2: Horner-Wadsworth-Emmons reaction / 6.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ol061439k

upstream raw materials:

(2R)-1-{(2R,4R,6R,8R,9S)-4-[tert-butyl(diphenyl)silyloxy]-8,9-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-3-methylbut-3-en-2-ol

allyl bromide

6-(4-methoxyphenoxy)hex-1-yne

ethyl 7-(4-methoxyphenoxy)hepta-2,4-dienoate

Downstream raw materials:

2-<(5R)-9-<(2R,4R,6R,8R,9S)-4-hydroxy-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-1-yl>-1,5,7-trimethyl-1(E),3(E),7(Z)-nonatrien-1-yl>-4-methoxy-5-methylbenzoic acid