(1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one

Base Information

• Chemical Name: (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one
• CAS No.: 211988-76-0
• Molecular Formula: C₂₅H₃₈O₅SSi
• Molecular Weight: 478.725
• Mol file: 211988-76-0.mol

Synonyms:(1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one

Chemical Property of (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one

There total 13 articles about (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one 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: 88.0%

(1R,2Z,7S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(2S)-5-oxo-4-(phenylsulfonyl)tetrahydro-2-furanyl]methyl-2-octenyl 4-methoxybenzoate (211988-77-1) → (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one (211988-76-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; Heating;

DOI:10.1016/S0040-4039(98)01078-8

Reference yield:

ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate (105198-38-7,106513-42-2) → (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one (211988-76-0)

Guidance literature:

Multi-step reaction with 14 steps

1: DIBAL / CH₂Cl₂ / -78 °C

2: LiCl, iPr₂NEt / acetonitrile

3: H₂ / Pd/C / ethanol

4: DIBAL / CH₂Cl₂ / -78 °C

5: Et₃N, 4-DMAP / CH₂Cl₂

6: dimethylsulfoxide

7: 81 percent / n-BuLi / tetrahydrofuran / -78 °C

8: 95 percent / H₂, quinoline / Lindlar catalyst / methanol

9: 95 percent / LAH, LiI / diethyl ether / -78 °C

10: 84 percent / CSA / CH₂Cl₂

11: 99 percent / Et₃N, 4-DMAP / CH₂Cl₂

12: 72 percent / NaH / dimethylformamide / 100 °C

13: 1.) DDQ; 2.) DBU / 1.) CH₂Cl₂/H₂O; 2.) MeCN

14: 88 percent / Pd(PPh₃)4, DBU / tetrahydrofuran / Heating

With quinoline; dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium iodide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)01078-8

Reference yield:

(S)-2-tert-butyl-dimethyl-silanyloxy propanal (87727-28-4) → (1S,4R,5S)-4-Benzenesulfonyl-5-[(E)-(S)-6-(tert-butyl-dimethyl-silanyloxy)-hept-1-enyl]-2-oxa-bicyclo[2.2.1]heptan-3-one (211988-76-0)

Guidance literature:

Multi-step reaction with 13 steps

1: LiCl, iPr₂NEt / acetonitrile

2: H₂ / Pd/C / ethanol

3: DIBAL / CH₂Cl₂ / -78 °C

4: Et₃N, 4-DMAP / CH₂Cl₂

5: dimethylsulfoxide

6: 81 percent / n-BuLi / tetrahydrofuran / -78 °C

7: 95 percent / H₂, quinoline / Lindlar catalyst / methanol

8: 95 percent / LAH, LiI / diethyl ether / -78 °C

9: 84 percent / CSA / CH₂Cl₂

10: 99 percent / Et₃N, 4-DMAP / CH₂Cl₂

11: 72 percent / NaH / dimethylformamide / 100 °C

12: 1.) DDQ; 2.) DBU / 1.) CH₂Cl₂/H₂O; 2.) MeCN

13: 88 percent / Pd(PPh₃)4, DBU / tetrahydrofuran / Heating

With quinoline; dmap; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; lithium iodide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(98)01078-8

upstream raw materials:

(1R,2Z,7S)-7-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-1-[(2S)-5-oxo-4-(phenylsulfonyl)tetrahydro-2-furanyl]methyl-2-octenyl 4-methoxybenzoate

ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

(S)-(+)-6-((tert-butyldimethylsilyl)oxy)-1-heptyne