(3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol

Base Information

• Chemical Name: (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol
• CAS No.: 853995-91-2
• Molecular Formula: C₄₅H₈₂O₆Si₂
• Molecular Weight: 775.313
• Mol file: 853995-91-2.mol

Synonyms:(3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol

Chemical Property of (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol

There total 23 articles about (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-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: 60.0%

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran (853995-86-5) + 2-((1S,3S)-1,3,5-Trimethyl-hex-5-enyl)-oxirane (638188-61-1) → (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol (853995-91-2)

Guidance literature:

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.0833333h;

2-((1S,3S)-1,3,5-Trimethyl-hex-5-enyl)-oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; pentane; at -78 ℃; for 3h;

DOI:10.1021/ja051420x

Reference yield:

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran (853995-86-5) + 2-((1S,3S)-1,3,5-Trimethyl-hex-5-enyl)-oxirane (638188-61-1) → (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol (853995-91-2) + (2R,3S,4S,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran

Guidance literature:

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran; With n-butyllithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.0833333h;

2-((1S,3S)-1,3,5-Trimethyl-hex-5-enyl)-oxirane; With boron trifluoride diethyl etherate; In tetrahydrofuran; pentane; at -78 ℃; for 3h;

DOI:10.1021/ja060369+

Reference yield:

(2S,3R,6S)-3-Hydroxy-2,6-dimethyl-oct-7-enoic acid (853995-88-7) → (3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol (853995-91-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

2.1: 85 percent / tetrahydrofuran / 24 h / Heating

3.1: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

4.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C

4.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C

5.1: 81 percent / NaBH₄ / ethanol / 2.5 h / -78 °C

6.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -10 °C

7.1: n-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C

7.2: BF₃*Et₂O / tetrahydrofuran; pentane / 3 h / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; pentane; 1.1: Kurihara condensation / 2.1: Petasis-Tebbe reaction / 3.1: Petasis-Ferrier rearrangement;

DOI:10.1021/ja060369+

upstream raw materials:

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran

2-((1S,3S)-1,3,5-Trimethyl-hex-5-enyl)-oxirane

(2S,3R,6S)-3-Hydroxy-2,6-dimethyl-oct-7-enoic acid

2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde

Downstream raw materials:

(5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one