Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester

Base Information

• Chemical Name: Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester
• CAS No.: 1027414-45-4
• Molecular Formula: C₂₈H₃₈O₇SSi
• Molecular Weight: 546.757
• Mol file: 1027414-45-4.mol

Synonyms:

Chemical Property of Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester

There total 8 articles about Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester 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:

methanesulfonyl chloride (124-63-0) + 5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one (1026583-53-8) → Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester (1027414-45-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo961993f

Reference yield:

4-methoxy-3-methyl-2(5H)-furanone (27205-80-7) → Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester (1027414-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

2: Et₃N, DMAP / CH₂Cl₂ / 0.08 h / 0 °C

With dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/jo961993f

Reference yield:

(S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile (88557-55-5,110171-23-8,143900-00-9,143900-08-7) → Methanesulfonic acid (S)-4-(tert-butyl-diphenyl-silanyloxy)-1-(3-methoxy-4-methyl-5-oxo-2,5-dihydro-furan-2-yl)-2-methyl-butyl ester (1027414-45-4)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL-H / CH₂Cl₂ / 0.08 h / -78 °C

2: 7.44 g / NaBH₄ / diethyl ether; methanol / 0.08 h / Ambient temperature

3: DMAP / CH₂Cl₂ / 0.08 h / Ambient temperature

4: 91 percent / Bu₂Sn(SMe)2, BF₃*OEt / CH₂Cl₂ / 0.08 h / 0 °C

5: 95 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / -78 deg C, 40 min, 0 deg C, 30 min

6: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.33 h / -78 °C

7: Et₃N, DMAP / CH₂Cl₂ / 0.08 h / 0 °C

With dmap; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; Dibutyl-bis-methylmercapto-zinn; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/jo961993f

upstream raw materials:

methanesulfonyl chloride

5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-methyl-butyl]-4-methoxy-3-methyl-5H-furan-2-one

4-methoxy-3-methyl-2(5H)-furanone

(S)-(-)-3-methyl-4-<(2-tetrahydropyranyl)oxy>butyronitrile

Downstream raw materials:

C₃₃H₃₈O₆S

(-)-ircinianin

5-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-but-(Z)-ylidene]-4-methoxy-3-methyl-5H-furan-2-one