(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine

Base Information

• Chemical Name: (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine
• CAS No.: 600728-65-2
• Molecular Formula: C₃₁H₅₀O₃Si₂
• Molecular Weight: 526.907
• Mol file: 600728-65-2.mol

Synonyms:(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine

Chemical Property of (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine

There total 17 articles about (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine 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: 88.0%

trimethylsilylacetylene (1066-54-2) + {(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-4-iodo-but-3-enyloxy}-tert-butyl-dimethyl-silane (600728-64-1) → (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine (600728-65-2)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol034923l

Reference yield:

1,5-hexadiene-3-ol (924-41-4) → (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine (600728-65-2)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH₂Cl₂ / 40 h / -20 °C

2.1: PPTS / 0 - 20 °C

2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C

3.1: 94 percent / KH; Bu₄NI / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 °C

5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C

6.1: pivaloyl chloride; Et₃N / tetrahydrofuran / -78 - 0 °C

6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

7.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C

7.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C

8.1: 92 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

9.1: 96 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

10.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 5 °C

11.1: TiCl₄; (-)-sparteine; N-methylpyrroldinone / CH₂Cl₂ / 0.33 h / 0 °C

11.2: 92 percent / CH₂Cl₂ / 1 h / -78 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

13.1: 0.370 g / NaBH₄ / tetrahydrofuran; H₂O / 43 h / 20 °C

14.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 15 °C

15.1: NaN(SiMe₃)2; HMPA / tetrahydrofuran; toluene / -65 °C

15.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C

16.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh₃)4 / tetrahydrofuran / 0 - 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; (-)-dicyclohexyl D-tartrate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; pivaloyl chloride; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-sparteine; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: Sharpless kinetic resolution / 10.1: Swern oxidation / 14.1: Swern oxidation / 16.1: Sonogashira coupling;

DOI:10.1021/ol034923l

Reference yield:

(4R,5S)-5-benzyloxy-1-hepten-4-ol (99838-64-9) → (2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-[(Z)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-6-trimethylsilanyl-hex-3-en-5-ynyl]-2,3,6,7-tetrahydro-oxepine (600728-65-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 84 h / 20 °C

2.1: pivaloyl chloride; Et₃N / tetrahydrofuran / -78 - 0 °C

2.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

3.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C

3.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C

4.1: 92 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

5.1: 96 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

6.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 5 °C

7.1: TiCl₄; (-)-sparteine; N-methylpyrroldinone / CH₂Cl₂ / 0.33 h / 0 °C

7.2: 92 percent / CH₂Cl₂ / 1 h / -78 °C

8.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

9.1: 0.370 g / NaBH₄ / tetrahydrofuran; H₂O / 43 h / 20 °C

10.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 15 °C

11.1: NaN(SiMe₃)2; HMPA / tetrahydrofuran; toluene / -65 °C

11.2: 79 percent / tetrahydrofuran; toluene / 1 h / -78 °C

12.1: 88 percent / CuI; (i-Pr)2NEt / Pd(PPh₃)4 / tetrahydrofuran / 0 - 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; copper(l) iodide; oxalyl dichloride; sodium hexamethyldisilazane; pivaloyl chloride; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-sparteine; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; toluene; 6.1: Swern oxidation / 10.1: Swern oxidation / 12.1: Sonogashira coupling;

DOI:10.1021/ol034923l

upstream raw materials:

trimethylsilylacetylene

{(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-4-iodo-but-3-enyloxy}-tert-butyl-dimethyl-silane

1,5-hexadiene-3-ol

(4R,5S)-5-benzyloxy-1-hepten-4-ol

Downstream raw materials:

(2R,7R)-2-((S)-1-Benzyloxy-propyl)-7-((Z)-(R)-1-chloro-hex-3-en-5-ynyl)-2,3,6,7-tetrahydro-oxepine

(Z)-(S)-1-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-hex-3-en-5-yn-1-ol