1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol

Base Information

• Chemical Name: 1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol
• CAS No.: 257299-90-4
• Molecular Formula: C₁₇H₃₀O₄Si
• Molecular Weight: 326.508
• Mol file: 257299-90-4.mol

Synonyms:1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol

Chemical Property of 1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol

There total 1 articles about 1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-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: 92.0%

1-chloro-3,5-dimethoxybenzene (7051-16-3) + tert-butyldimethylsilyl (S)-glycidyl ether (78906-15-7,114413-26-2,124150-87-4,123237-62-7) → 1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol (257299-90-4)

Guidance literature:

1-chloro-3,5-dimethoxybenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; for 10h; Heating;

tert-butyldimethylsilyl (S)-glycidyl ether; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -20 ℃; for 4.5h;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol (257299-90-4) → [(1R,3S)-5-(4-Benzyloxy-5-methoxy-7-triisopropylsilanyloxymethyl-naphthalen-1-yl)-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

Guidance literature:

Multi-step reaction with 12 steps

1.1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C

2.1: 89 percent / H₂NNH₂ / ethanol / 7 h / Heating

3.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

4.1: 97 percent / POCl₃; 2,4,6-collidine / acetonitrile / 3 h / 85 °C

5.1: LiAlH₄; Me₃Al / tetrahydrofuran; hexane / -78 - 20 °C

6.1: NaH / tetrahydrofuran

6.2: 85 percent / tetrahydrofuran / -78 °C

7.1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

8.1: 89 percent / I₂; PhI(O₂CCF₃)2 / CH₂Cl₂ / -10 - 0 °C

9.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

10.1: 99 percent / DCC / CH₂Cl₂ / 14 h / 20 °C

11.1: 81 percent / K₃PO₄; 2,6-di-tert-butyl-4-methylphenol / [Pd(dppf)Cl₂] / dimethylformamide / 117 °C

12.1: 85 percent / NaOH; MeOH / 20 °C

With 2,4,6-trimethyl-pyridine; methanol; sodium hydroxide; potassium phosphate; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; iodine; trimethylaluminum; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; hydrazine; diethylazodicarboxylate; trichlorophosphate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Mitsunobu reaction / 2.1: Hydrazinolysis / 3.1: Acetylation / 4.1: Bischler-Napieralski cyclization / 5.1: Reduction / 6.1: Metallation / 6.2: Etherification / 7.1: Tosylation / 8.1: Iodination / 9.1: Desilylation / 10.1: Esterification / 11.1: Arylation / 12.1: Saponification;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)-3-(3,5-dimethoxy-phenyl)-propan-2-ol (257299-90-4) → (1R,3S)-5-(4-Benzyloxy-5-methoxy-7-triisopropylsilanyloxymethyl-naphthalen-1-yl)-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline

Guidance literature:

Multi-step reaction with 9 steps

1.1: 88 percent / PPh₃; DEAD / tetrahydrofuran / 20 h / 0 - 20 °C

2.1: 89 percent / H₂NNH₂ / ethanol / 7 h / Heating

3.1: 99 percent / NEt₃ / CH₂Cl₂ / 20 °C

4.1: 97 percent / POCl₃; 2,4,6-collidine / acetonitrile / 3 h / 85 °C

5.1: LiAlH₄; Me₃Al / tetrahydrofuran; hexane / -78 - 20 °C

6.1: NaH / tetrahydrofuran

6.2: 85 percent / tetrahydrofuran / -78 °C

7.1: 93 percent / NEt₃ / CH₂Cl₂ / 20 °C

8.1: 89 percent / I₂; PhI(O₂CCF₃)2 / CH₂Cl₂ / -10 - 0 °C

9.1: 81 percent / K₃PO₄; 2,6-di-tert-butyl-4-methylphenol / [Pd(PPh₃)4] / dimethylformamide / 96 °C

With 2,4,6-trimethyl-pyridine; potassium phosphate; lithium aluminium tetrahydride; 2,6-di-tert-butyl-4-methyl-phenol; iodine; trimethylaluminum; sodium hydride; triethylamine; triphenylphosphine; bis-[(trifluoroacetoxy)iodo]benzene; hydrazine; diethylazodicarboxylate; trichlorophosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Mitsunobu reaction / 2.1: Hydrazinolysis / 3.1: Acetylation / 4.1: Bischler-Napieralski cyclization / 5.1: Reduction / 6.1: Metallation / 6.2: Etherification / 7.1: Tosylation / 8.1: Iodination / 9.1: Arylation;

DOI:10.1002/(SICI)1521-3773(19991203)38:23<3530::AID-ANIE3530>3.0.CO;2-W

upstream raw materials:

1-chloro-3,5-dimethoxybenzene

tert-butyldimethylsilyl (S)-glycidyl ether

Downstream raw materials:

2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethylamine

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-(3,5-dimethoxy-benzyl)-ethyl]-acetamide

[(1R,3S)-5-Iodo-6,8-dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-3-yl]-methanol

(1R,3S)-6,8-Dimethoxy-1-methyl-2-(toluene-4-sulfonyl)-3-triisopropylsilanyloxymethyl-1,2,3,4-tetrahydro-isoquinoline