Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester

Base Information

• Chemical Name: Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester
• CAS No.: 320742-74-3
• Molecular Formula: C₂₅H₃₈O₄SSi
• Molecular Weight: 462.726
• Mol file: 320742-74-3.mol

Synonyms:Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester

Chemical Property of Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester

There total 6 articles about Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl 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:

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol (128329-63-5) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester (320742-74-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja005526y DOI:10.1016/j.tet.2004.06.014

Reference yield:

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol (198124-61-7) → Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester (320742-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

3.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

3.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester (321162-62-3) → Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester (320742-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

2.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.06.014

upstream raw materials:

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol

methanesulfonyl chloride

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

(2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

Downstream raw materials:

(3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexylamine

(+)-kalkitoxin

(R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

(2R)-N-methyl-N-[(3S,5S)-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide