[(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane
• CAS No.: 136088-41-0
• Molecular Formula: C₂₀H₃₄O₃SSi
• Molecular Weight: 382.64

Synonyms:[(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property of [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane

There total 12 articles about [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-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: 89.0%

tert-Butyl-dimethyl-[(E)-(S)-2-methyl-1-((R)-1-methyl-2-phenylsulfanyl-ethyl)-but-2-enyloxy]-silane → [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane (136088-41-0)

Guidance literature:

With diphenyl diselenide; dihydrogen peroxide; In diethyl ether; dichloromethane; at 22 ℃; for 4h;

Reference yield:

O1,O2;O5,O6-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose (21665-16-7) → [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane (136088-41-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / H₂, Et₃N / 10percent Pd/C / methanol / 5 h / 22 °C

2: 84 percent / 0.1 N H₂SO₄ / methanol / 5 h / 22 °C

3: 93 percent / pyridine / 20 h / 22 °C

4: 88 percent / LiAlH₄ / diethyl ether / 3 h / 35 °C

5: 93 percent / pyridiniumchloromate, Al₂O₃, NaOAc / CH₂Cl₂ / 24 h / 22 °C

6: nBuLi, (PhS)2 / tetrahydrofuran; benzene / 2.5 h / 22 °C / Irradiation

7: 76 percent / 1.4 N H₂SO₄ / dioxane / 48 h / 22 °C

9: 93 percent / pyridine / 20 h / 22 °C

10: 92 percent / imidazole / dimethylformamide / 15 h / 22 °C

11: 75 percent / KOtBu / dimethylformamide / 1 h / 45 °C

12: 89 percent / (PhSe)2, 15 percent H₂O₂ / CH₂Cl₂; diethyl ether / 4 h / 22 °C

With pyridine; 1H-imidazole; aluminum oxide; lithium aluminium tetrahydride; n-butyllithium; pyridiniumchloromate; sulfuric acid; diphenyl diselenide; potassium tert-butylate; hydrogen; dihydrogen peroxide; sodium acetate; triethylamine; diphenyldisulfane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

Reference yield:

(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol (26291-75-8,81114-49-0,109200-09-1,128461-80-3) → [(E)-(S)-1-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2-methyl-but-2-enyloxy]-tert-butyl-dimethyl-silane (136088-41-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / pyridine / 20 h / 22 °C

2: 88 percent / LiAlH₄ / diethyl ether / 3 h / 35 °C

3: 93 percent / pyridiniumchloromate, Al₂O₃, NaOAc / CH₂Cl₂ / 24 h / 22 °C

4: nBuLi, (PhS)2 / tetrahydrofuran; benzene / 2.5 h / 22 °C / Irradiation

5: 76 percent / 1.4 N H₂SO₄ / dioxane / 48 h / 22 °C

7: 93 percent / pyridine / 20 h / 22 °C

8: 92 percent / imidazole / dimethylformamide / 15 h / 22 °C

9: 75 percent / KOtBu / dimethylformamide / 1 h / 45 °C

10: 89 percent / (PhSe)2, 15 percent H₂O₂ / CH₂Cl₂; diethyl ether / 4 h / 22 °C

With pyridine; 1H-imidazole; aluminum oxide; lithium aluminium tetrahydride; n-butyllithium; pyridiniumchloromate; sulfuric acid; diphenyl diselenide; potassium tert-butylate; dihydrogen peroxide; sodium acetate; diphenyldisulfane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

upstream raw materials:

(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2,6-trimethyl-tetrahydrofuro[2,3-d][1,3]dioxole

O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose

(R)-2-hydroxy-2-((3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl4-methylbenzenesulfonate

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