(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

Base Information

• Chemical Name: (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
• CAS No.: 503071-63-4
• Molecular Formula: C₃₈H₅₆O₄Si
• Molecular Weight: 604.946
• Mol file: 503071-63-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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: 70.0%

allyl methoxymethyl ether (62322-45-6) + {(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}acetaldehyde (402827-64-9) → (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) + (2R,3R)-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 (503071-64-5)

Guidance literature:

allyl methoxymethyl ether; With sec.-butyllithium; (-)-B-methoxy-diisopinocamphenylborane; In tetrahydrofuran; cyclohexane; at -78 ℃; for 1h;

{(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}acetaldehyde; With boron trifluoride diethyl etherate; In tetrahydrofuran; cyclohexane; at -78 ℃; for 5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; cyclohexane; at 20 ℃;

DOI:10.1016/j.tet.2003.08.057

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (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)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2.1: 99 percent / AcOH / H₂O; tetrahydrofuran / 21 h / 20 °C

3.1: 98 percent / NaBH₄ / ethanol / 0.25 h / 20 °C

4.1: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 95 percent / 18-crown-6 / acetonitrile / 6 h / 80 °C

6.1: DIBAL-H / toluene; hexane / 0.75 h / -78 °C

6.2: 100 percent / tartaric acid / H₂O; ethyl acetate; various solvents / 1 h / 20 °C

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

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

7.3: 70 percent / NaOH; H₂O₂ / tetrahydrofuran; cyclohexane / 20 °C

With 1H-imidazole; sodium tetrahydroborate; 18-crown-6 ether; sec.-butyllithium; diisobutylaluminium hydride; acetic acid; triethylamine; (-)-B-methoxy-diisopinocamphenylborane; In tetrahydrofuran; ethanol; hexane; dichloromethane; cyclohexane; water; toluene; acetonitrile; 7.2: Brown allylation;

DOI:10.1016/j.tet.2003.08.057

Reference yield:

[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetaldehyde (221290-57-9) → (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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: ¹Ipc₂BOMe / diethyl ether; tetrahydrofuran / 1 h / 20 °C

1.2: diethyl ether; tetrahydrofuran / 6 h / -78 °C

1.3: 77 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran; diethyl ether / 15 h / 20 °C

2.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3.1: 99 percent / AcOH / H₂O; tetrahydrofuran / 21 h / 20 °C

4.1: 98 percent / NaBH₄ / ethanol / 0.25 h / 20 °C

5.1: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: 95 percent / 18-crown-6 / acetonitrile / 6 h / 80 °C

7.1: DIBAL-H / toluene; hexane / 0.75 h / -78 °C

7.2: 100 percent / tartaric acid / H₂O; ethyl acetate; various solvents / 1 h / 20 °C

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

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

8.3: 70 percent / NaOH; H₂O₂ / tetrahydrofuran; cyclohexane / 20 °C

With 1H-imidazole; sodium tetrahydroborate; 18-crown-6 ether; sec.-butyllithium; diisobutylaluminium hydride; acetic acid; triethylamine; (-)-B-methoxy-diisopinocamphenylborane; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; cyclohexane; water; toluene; acetonitrile; 1.2: Brown allylation / 8.2: Brown allylation;

DOI:10.1016/j.tet.2003.08.057

upstream raw materials:

allyl methoxymethyl ether

{(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}acetaldehyde

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

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-acetoxy-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

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

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