(2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate
• CAS No.: 1374991-68-0
• Molecular Formula: C₃₀H₄₀O₆SSi
• Molecular Weight: 556.796

Synonyms:(2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate

Chemical Property of (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate

There total 7 articles about (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate 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:

C13H20O5 → (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate (1374991-68-0)

Guidance literature:

Multi-step reaction with 12 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 2 h

2: water; acetic acid / 12 h / 20 °C

3: sodium periodate / methanol / 2 h / 0 - 20 °C

4: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

5: 1H-imidazole / dichloromethane / 0.25 h / 0 °C

6: boron trichloride / dichloromethane / 0.03 h / 0 °C

7: sodium periodate / methanol; water / 0.5 h / 0 °C

8: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

9: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

10: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 - 20 °C

11: toluene-4-sulfonic acid / methanol / 0.5 h / 15 °C / Cooling with ice

12: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Cooling with ice

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; palladium 10% on activated carbon; water; hydrogen; boron trichloride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; ethanol; dichloromethane; water;

DOI:10.1016/j.tetasy.2012.03.005

Reference yield:

C21H28O3Si → (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate (1374991-68-0)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

2: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C

3: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 - 20 °C

4: toluene-4-sulfonic acid / methanol / 0.5 h / 15 °C / Cooling with ice

5: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Cooling with ice

With dmap; sodium tetrahydroborate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2012.03.005

Reference yield:

C27H44O3Si2 (1374991-73-7) → (2S,3S)-4-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-2-methylbutyl 4-methylbenzenesulfonate (1374991-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 - 20 °C

2: toluene-4-sulfonic acid / methanol / 0.5 h / 15 °C / Cooling with ice

3: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Cooling with ice

With dmap; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/j.tetasy.2012.03.005

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

C₂₇H₄₄O₃Si₂

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

Downstream raw materials:

(S)-5-((S)-hex-4-yn-2-yl)-9,9-dimethyl-8,8-diphenyl-2,4,7-trioxa-8-siladecane

C₂₃H₃₃IO₃Si

C₁₇H₂₂N₄O₂S

C₁₇H₂₂N₄O₄S

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