(4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol

Base Information

• Chemical Name: (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol
• CAS No.: 218439-25-9
• Molecular Formula: C₃₈H₅₂O₄S₂Si
• Molecular Weight: 665.046
• Mol file: 218439-25-9.mol

Synonyms:

Chemical Property of (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol

There total 12 articles about (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-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:

tert-butyl((1S,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-iodo-3-methylbutoxy)dimethylsilane (218439-40-8) → (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol (218439-25-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

2: 88 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

3: 100 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 50 °C

4: 83 percent / aq. AcOH / 0.33 h / 40 °C

5: 100 percent / PPTS / CH₂Cl₂

6: 73 percent / DIBAL-H / toluene / 0.5 h / -78 °C

7: 77 mg / DMSO, Et₃N, SO₃-pyridine / 1 h / Ambient temperature

8: 62 mg / tetrahydrofuran / 0.25 h / 0 - 5 °C

With 1H-imidazole; dmap; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1246/bcsj.71.2433

Reference yield:

(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol (218439-18-0) → (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol (218439-25-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / pyridine / Ambient temperature

2: 89 percent / NaI / acetone / Heating

3: 100 percent / t-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; pentane / 1 h / -78 °C

4: 88 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

5: 100 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 50 °C

6: 83 percent / aq. AcOH / 0.33 h / 40 °C

7: 100 percent / PPTS / CH₂Cl₂

8: 73 percent / DIBAL-H / toluene / 0.5 h / -78 °C

9: 77 mg / DMSO, Et₃N, SO₃-pyridine / 1 h / Ambient temperature

10: 62 mg / tetrahydrofuran / 0.25 h / 0 - 5 °C

With 1H-imidazole; dmap; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; pentane;

DOI:10.1246/bcsj.71.2433

Reference yield:

(1S,3S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-methyl-4-(2-methyl-[1,3]dithian-2-yl)-butan-1-ol (218439-41-9) → (4R,5S,7S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-7-methyl-8-(2-methyl-[1,3]dithian-2-yl)-oct-1-en-3-ol (218439-25-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 50 °C

2: 83 percent / aq. AcOH / 0.33 h / 40 °C

3: 100 percent / PPTS / CH₂Cl₂

4: 73 percent / DIBAL-H / toluene / 0.5 h / -78 °C

5: 77 mg / DMSO, Et₃N, SO₃-pyridine / 1 h / Ambient temperature

6: 62 mg / tetrahydrofuran / 0.25 h / 0 - 5 °C

With 1H-imidazole; dmap; pyridine-SO₃ complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1246/bcsj.71.2433

upstream raw materials:

vinyl magnesium bromide

(2S,3S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-methyl-6-(2-methyl-[1,3]dithian-2-yl)-hexanal

tert-butyl((1S,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-iodo-3-methylbutoxy)dimethylsilane

(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butan-1-ol

Downstream raw materials:

(E)-(6R,7S,9S)-7-(tert-Butyl-diphenyl-silanyloxy)-6-(4-methoxy-benzyloxy)-9-methyl-10-(2-methyl-[1,3]dithian-2-yl)-dec-4-enal

tert-Butyl-{(1S,2R)-2-(4-methoxy-benzyloxy)-1-[(S)-2-methyl-3-(2-methyl-[1,3]dithian-2-yl)-propyl]-3-vinyloxy-pent-4-enyloxy}-diphenyl-silane