(E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol

Base Information

• Chemical Name: (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol
• CAS No.: 862557-38-8
• Molecular Formula: C₃₆H₆₂O₅Si
• Molecular Weight: 602.971
• Mol file: 862557-38-8.mol

Synonyms:

Chemical Property of (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol

There total 10 articles about (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-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:

(4E,8E)-12-Benzyloxy-dodeca-4,8-dienal (862557-97-9) → (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol (862557-38-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

3.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

3.2: tetrahydrofuran; hexane / 3 h / Heating

3.3: PTSA*H₂O / benzene / 1 h / Heating

4.1: trifluoroacetic anhydride; Re₂O₇ / CH₂Cl₂ / 6 h / 0 - 20 °C

5.1: lutidine / CH₂Cl₂ / 0.5 h

6.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h

7.2: tetrahydrofuran; hexane / 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; lutidine; diisobutylaluminium hydride; rhenium(VII) oxide; diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 2.1: Sharpless asymmetric epoxidation / 7.2: Wittig reaction;

DOI:10.1021/jo050697c

Reference yield:

(4E,8E)-12-Benzyloxy-dodeca-4,8-dien-1-ol (862557-57-1) → (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol (862557-38-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 91 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

3.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

4.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

4.2: tetrahydrofuran; hexane / 3 h / Heating

4.3: PTSA*H₂O / benzene / 1 h / Heating

5.1: trifluoroacetic anhydride; Re₂O₇ / CH₂Cl₂ / 6 h / 0 - 20 °C

6.1: lutidine / CH₂Cl₂ / 0.5 h

7.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h

8.2: tetrahydrofuran; hexane / 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; lutidine; diisobutylaluminium hydride; rhenium(VII) oxide; dimethyl sulfoxide; triethylamine; diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 8.2: Wittig reaction;

DOI:10.1021/jo050697c

Reference yield:

(6E,10E)-14-Benzyloxy-tetradeca-1,6,10-trien-3-ol (862557-60-6) → (E)-(R)-1-{(2S,5S,2'S,5'R)-5'-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-octahydro-[2,2']bifuranyl-5-yl}-undec-4-en-1-ol (862557-38-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

2.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

2.2: tetrahydrofuran; hexane / 3 h / Heating

2.3: PTSA*H₂O / benzene / 1 h / Heating

3.1: trifluoroacetic anhydride; Re₂O₇ / CH₂Cl₂ / 6 h / 0 - 20 °C

4.1: lutidine / CH₂Cl₂ / 0.5 h

5.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h

6.2: tetrahydrofuran; hexane / 0.5 h

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; lutidine; diisobutylaluminium hydride; rhenium(VII) oxide; diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Sharpless asymmetric epoxidation / 6.2: Wittig reaction;

DOI:10.1021/jo050697c

upstream raw materials:

triphenylheptylphosphonium bromide

(4E,8E)-12-Benzyloxy-dodeca-4,8-dienal

(4E,8E)-12-Benzyloxy-dodeca-4,8-dien-1-ol

(6E,10E)-14-Benzyloxy-tetradeca-1,6,10-trien-3-ol

Downstream raw materials:

(2S,5R,2'S,5'S)-5-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-5'-[(E)-(R)-1-(tert-butyl-dimethyl-silanyloxy)-undec-4-enyl]-octahydro-[2,2']bifuranyl