(R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

Base Information

• Chemical Name: (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol
• CAS No.: 790699-83-1
• Molecular Formula: C₃₅H₄₈O₄Si
• Molecular Weight: 560.849
• Mol file: 790699-83-1.mol

Synonyms:(R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

Chemical Property of (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol

There total 14 articles about (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-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:

(E)-(3R,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-ol (790699-79-5) → (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol (790699-83-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 0.75h;

DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

benzyl bromide (100-39-0) → (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol (790699-83-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 92 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1.5 h / 0 °C

2.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

7.2: tetrahydrofuran / 1 h / -78 - 0 °C

8.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

9.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

10.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

3-(tert-butyldiphenylsilyloxy)propan-1-ol (127047-71-6) → (R)-1-[(2S,3S)-3-((S)-4-Benzyloxy-hexyl)-2-methyl-oxiranyl]-3-(tert-butyl-diphenyl-silanyloxy)-propan-1-ol (790699-83-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂

1.2: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol

1.3: 82 percent / diethyl ether

2.1: 62 percent / BuLi / tetrahydrofuran

3.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.2: tetrahydrofuran / 1 h / -78 - 0 °C

4.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

5.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

6.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; dichloromethane; 3.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

upstream raw materials:

(E)-(3R,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undec-4-en-3-ol

benzyl bromide

3-(tert-butyldiphenylsilyloxy)propan-1-ol

methyl 3-<(tert-butyldiphenylsilyl)oxy>propionate

Downstream raw materials:

(3R,4R,5S,9S)-9-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undecane-3,5-diol

(4R,5S,6S)-6-((S)-4-Benzyloxy-hexyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-one

2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol

[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester