1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one

Base Information

• Chemical Name: 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one
• CAS No.: 233751-83-2
• Molecular Formula: C₃₀H₄₈O₅Si
• Molecular Weight: 516.794
• Mol file: 233751-83-2.mol

Synonyms:

Chemical Property of 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one

There total 10 articles about 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one 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: 40.0%

C48H79NO7SSi2 (233751-80-9) → 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one (233751-83-2) + 1-[2-(tert-Butyl-dimethyl-silanyloxy)-3-((1R,5S,6S,8R)-9,9-dimethyl-4,4-dioxo-4λ6-thia-tricyclo[6.1.1.02,6]dec-2-en-5-yl)-4,6-dimethoxy-phenyl]-3-methyl-butan-1-one (233751-84-3)

Guidance literature:

With aluminum amalgam; In tetrahydrofuran; water; for 15h;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1011::AID-EJOC1011>3.0.CO;2-H

Reference yield:

2-hydroxy-4,6-dimethoxybenzaldehyde (708-76-9) → 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one (233751-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / AlCl₃ / CH₂Cl₂ / 20 h / Ambient temperature

2: 76 percent / ethyldimethylamine, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

3: 1.) n-BuLi, ClTi(OiPr)3 / 1.) THF, hexane, 5 min, -78 deg C to 0 deg C, 60 min; 2.) THF, hexane, -78 deg C, 2 h

4: 21 percent / Al/Hg / tetrahydrofuran; H₂O / 15 h

With triisopropoxytitanium(IV) chloride; dmap; aluminum amalgam; n-butyllithium; aluminium trichloride; N,N-dimethyl-ethanamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1011::AID-EJOC1011>3.0.CO;2-H

Reference yield:

(-)-myrtenyl bromide (55527-89-4) → 1-{2-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-((1R,3S,5R)-6,6-dimethyl-2-methylene-bicyclo[3.1.1]hept-3-yl)-hydroxy-methyl]-4,6-dimethoxy-phenyl}-3-methyl-butan-1-one (233751-83-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄ / ethanol

2: 1.) tBuLi; 2.) Me₂NEt

3: 1.) n-BuLi, ClTi(OiPr)3 / 1.) THF, hexane, 5 min, -78 deg C to 0 deg C, 60 min; 2.) THF, hexane, -78 deg C, 2 h

4: 21 percent / Al/Hg / tetrahydrofuran; H₂O / 15 h

With triisopropoxytitanium(IV) chloride; sodium tetrahydroborate; aluminum amalgam; n-butyllithium; N,N-dimethyl-ethanamine; tert.-butyl lithium; In tetrahydrofuran; ethanol; water;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1011::AID-EJOC1011>3.0.CO;2-H

upstream raw materials:

C₄₈H₇₉NO₇SSi₂

2-hydroxy-4,6-dimethoxybenzaldehyde

(-)-myrtenyl bromide

(1R)-Myrtenol