[(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 558459-33-9
• Molecular Formula: C₂₈H₄₅BrO₃Si
• Molecular Weight: 537.653
• Mol file: 558459-33-9.mol

Synonyms:[(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane

There total 11 articles about [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane 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: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + (Z)-(4R,5S)-5-((1S,2R)-2-Benzyloxy-1-ethyl-pent-4-enyloxy)-8-bromo-octa-1,7-dien-4-ol (558459-32-8) → [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane (558459-33-9)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1021/ja029956v

Reference yield:

1,5-hexadiene-3-ol (924-41-4) → [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane (558459-33-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (-)-dicyclohexyl tartrate; Ti(OiPr)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

1.2: 42 percent / t-BuOOH / CH₂Cl₂ / 19 h / -20 °C

2.1: 87 percent / Bu₄NI; NaH / tetrahydrofuran / -78 - 25 °C

3.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C

4.1: NaH / tetrahydrofuran / 0 - 25 °C

4.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

5.1: Et₃N / diethyl ether / -78 - 0 °C

6.1: n-BuLi / tetrahydrofuran; hexane

6.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

7.1: NaN(SiMe₃)2 / tetrahydrofuran / -78 - -45 °C

7.2: 85 percent / tetrahydrofuran

8.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O

9.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

10.1: 92 percent / diethyl ether / -78 °C

11.1: 90 percent / Et₃N / CH₂Cl₂

With titanium(IV) isopropylate; sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; (-)-dicyclohexyl D-tartrate; 4 A molecular sieve; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 9.1: Swern oxidation;

DOI:10.1021/ja029956v

Reference yield:

(1R)-1-[(1S)-oxiranyl]-but-3-en-1-ol (558459-27-1) → [(Z)-(1R,2S)-1-Allyl-2-((1S,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-5-bromo-pent-4-enyloxy]-tert-butyl-dimethyl-silane (558459-33-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 87 percent / Bu₄NI; NaH / tetrahydrofuran / -78 - 25 °C

2.1: 90 percent / CuI / tetrahydrofuran; diethyl ether / 1 h / -20 °C

3.1: NaH / tetrahydrofuran / 0 - 25 °C

3.2: 90 percent / tetrahydrofuran / 10 h / 25 °C

4.1: Et₃N / diethyl ether / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; hexane

5.2: 28.6 g / tetrahydrofuran; hexane / -78 - 0 °C

6.1: NaN(SiMe₃)2 / tetrahydrofuran / -78 - -45 °C

6.2: 85 percent / tetrahydrofuran

7.1: 82 percent / NaBH₄ / tetrahydrofuran; H₂O

8.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂

9.1: 92 percent / diethyl ether / -78 °C

10.1: 90 percent / Et₃N / CH₂Cl₂

With sodium tetrahydroborate; copper(l) iodide; n-butyllithium; oxalyl dichloride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; 8.1: Swern oxidation;

DOI:10.1021/ja029956v

upstream raw materials:

t-butyldimethylsiyl triflate

(Z)-(4R,5S)-5-((1S,2R)-2-Benzyloxy-1-ethyl-pent-4-enyloxy)-8-bromo-octa-1,7-dien-4-ol

1,5-hexadiene-3-ol

(1R)-1-[(1S)-oxiranyl]-but-3-en-1-ol