(S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

Base Information

• Chemical Name: (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol
• CAS No.: 600728-63-0
• Molecular Formula: C₂₅H₄₂O₄Si
• Molecular Weight: 434.692
• Mol file: 600728-63-0.mol

Synonyms:(S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

Chemical Property of (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

There total 14 articles about (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-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:

1,5-hexadiene-3-ol (924-41-4) → (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (600728-63-0)

Guidance literature:

Multi-step reaction with 13 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

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; 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; (-)-sparteine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: Sharpless kinetic resolution / 10.1: Swern oxidation;

DOI:10.1021/ol034923l

Reference yield:

(4R,5S)-5-benzyloxy-1-hepten-4-ol (99838-64-9) → (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (600728-63-0)

Guidance literature:

Multi-step reaction with 9 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

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; sodium tetrahydroborate; oxalyl dichloride; sodium hexamethyldisilazane; pivaloyl chloride; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; (-)-sparteine; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; toluene; 6.1: Swern oxidation;

DOI:10.1021/ol034923l

Reference yield:

(1R)-1-[(1S)-oxiranyl]-but-3-en-1-ol (558459-27-1) → (S)-3-[(2R,7R)-7-((S)-1-Benzyloxy-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (600728-63-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: PPTS / 0 - 20 °C

1.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C

2.1: 94 percent / KH; Bu₄NI / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: 91 percent / p-TsOH / methanol / 0 - 20 °C

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

4.2: 98 percent / tetrahydrofuran / 84 h / 20 °C

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

5.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

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

6.2: 86 percent / toluene; tetrahydrofuran / -78 - -45 °C

7.1: 92 percent / NaBH₄ / tetrahydrofuran; H₂O / 0 - 20 °C

8.1: 96 percent / (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

9.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 5 °C

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

10.2: 92 percent / CH₂Cl₂ / 1 h / -78 °C

11.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

12.1: 0.370 g / NaBH₄ / tetrahydrofuran; H₂O / 43 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; sodium tetrahydroborate; oxalyl dichloride; 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; (-)-sparteine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 9.1: Swern oxidation;

DOI:10.1021/ol034923l

upstream raw materials:

1,5-hexadiene-3-ol

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

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

(3S,4R)-4-(Tetrahydro-pyran-2-yloxy)-hept-6-en-3-ol

Downstream raw materials:

(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

{(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

(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

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