(1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

Base Information

• Chemical Name: (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol
• CAS No.: 906076-73-1
• Molecular Formula: C₂₁H₃₄O₄SSi
• Molecular Weight: 410.65
• Mol file: 906076-73-1.mol

Synonyms:(1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

Chemical Property of (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol

There total 4 articles about (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol 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: 95.0%

(1S,4R,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-4-(3,5-dimethyl-pyrazol-1-yl)-7-methyl-cyclohept-2-enol (906076-71-9) + methylmagnesium bromide (75-16-1) → (1S,2R,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol + (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol (906076-73-1)

Guidance literature:

In tetrahydrofuran; toluene; at 20 ℃; for 0.5h;

DOI:10.1021/ol060530l

Reference yield:

((1R,2R)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane (606129-09-3) → (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol (906076-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 68 percent / Oxone(R); NaHCO₃ / (R,R)-Jacobsen's catalyst / acetone

2.1: 3,5-dimethylpyrazole / toluene / 3 h / 65 °C

2.2: toluene; tetrahydrofuran / 1 h / 36 °C

With 3,5-dimethyl-1H-pyrazole; oxone; sodium hydrogencarbonate; (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III); In acetone; toluene;

DOI:10.1021/ja071217x

Reference yield:

tert-butyldimethyl(((1S,2R,3R,7S)-2-methyl-6-(phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-5-en-3-yl)oxy)silane (906076-69-5) + methylmagnesium bromide (75-16-1) → (1S,2R,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol + (1S,2S,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2,7-dimethyl-cyclohept-3-enol (906076-73-1)

Guidance literature:

tert-butyldimethyl(((1S,2R,3R,7S)-2-methyl-6-(phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-5-en-3-yl)oxy)silane; With 3,5-dimethyl-1H-pyrazole; In toluene; at 65 ℃; for 3h;

methylmagnesium bromide; In tetrahydrofuran; toluene; at 36 ℃; for 1h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ja071217x

upstream raw materials:

(1S,4R,6R,7R)-3-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-4-(3,5-dimethyl-pyrazol-1-yl)-7-methyl-cyclohept-2-enol

methylmagnesium bromide

tert-butyldimethyl(((1S,2R,3R,7S)-2-methyl-6-(phenylsulfonyl)-8-oxabicyclo[5.1.0]oct-5-en-3-yl)oxy)silane

((1R,2R)-5-Benzenesulfonyl-2-methyl-cyclohepta-3,5-dienyloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(4R,5S,6S,7S)-1-Benzenesulfonyl-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-5,7-dimethyl-cycloheptene

(1R,5S,6S,7S)-6-(tert-butyldimethylsilyloxy)-5,7-dimethyl-4-(phenylsulfonyl)cyclohept-3-enol