2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester

Base Information

• Chemical Name: 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester
• CAS No.: 503071-66-7
• Molecular Formula: C₄₁H₆₀O₄Si
• Molecular Weight: 645.01
• Mol file: 503071-66-7.mol

Synonyms:2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester

Chemical Property of 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester

There total 12 articles about 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester 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: 64.0%

2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-methoxymethoxybut-3-enyl ester (503071-65-6) → 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester (503071-66-7)

Guidance literature:

With boron trifluoride diethyl etherate; thiophenol; In dichloromethane; at -78 - -10 ℃;

DOI:10.1016/S0040-4039(02)02646-1

Reference yield:

{(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}acetaldehyde (402827-64-9) → 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester (503071-66-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sec-BuLi; ¹Ipc₂BOMe / tetrahydrofuran; cyclohexane / 1 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran; cyclohexane / 5 h / -78 °C

1.3: 70 percent / NaOH; H₂O₂ / tetrahydrofuran; cyclohexane / 20 °C

2.1: 80 percent / pyridine; 4-(dimethylamino)pyridine / 72 h / 20 °C

3.1: 64 percent / PhSH; BF₃*Et₂O / CH₂Cl₂ / -78 - -10 °C

With pyridine; dmap; boron trifluoride diethyl etherate; sec.-butyllithium; thiophenol; (-)-B-methoxy-diisopinocamphenylborane; In tetrahydrofuran; dichloromethane; cyclohexane; 1.2: Brown allylation;

DOI:10.1016/j.tet.2003.08.057

Reference yield:

(2S,3S)-1-{(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}-3-methoxymethoxypent-4-en-2-ol (503071-63-4) → 2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-hydroxybut-3-enyl ester (503071-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridine; 4-(dimethylamino)pyridine / 72 h / 20 °C

2: 64 percent / PhSH; BF₃*Et₂O / CH₂Cl₂ / -78 - -10 °C

With pyridine; dmap; boron trifluoride diethyl etherate; thiophenol; In dichloromethane;

DOI:10.1016/j.tet.2003.08.057

upstream raw materials:

2,2-dimethylpropionic acid (1S,2S)-1-{[(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl]methyl}-2-methoxymethoxybut-3-enyl ester

tert-butylchlorodiphenylsilane

[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetaldehyde

(2R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methylcyclohex-2-enyl]pent-4-en-2-ol

Downstream raw materials:

2,2-dimethylpropionic acid (4R,4aR,6S,7S,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-7-methoxy-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

2,2-dimethylpropionic acid (4R,4aR,6S,7S,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-7-acetoxy-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

2,2-dimethylpropionic acid (4R,4aR,6S,7S,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-7-[(2'RS)-tetrahydropyran-2'-yloxy]-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

2,2-dimethylpropionic acid (4R,4aR,6S,7S,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-7-hydroxy-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester