(E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester

Base Information

• Chemical Name: (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester
• CAS No.: 370562-13-3
• Molecular Formula: C₂₆H₄₀O₅S
• Molecular Weight: 464.667
• Mol file: 370562-13-3.mol

Synonyms:(E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester

Chemical Property of (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester

There total 7 articles about (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-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:

(2S,3S)-tert-butyldimethylsilyl-2-methylhex-4-yn-3-ol → (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester (370562-13-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 92 percent / Ag₂O / diethyl ether / 3.5 h / 20 °C

2.1: 85 percent / CpRu(CH₃CN)3PF₆ / acetone / 0.33 h / 20 °C

3.1: 51 percent / Bu₄NCl / (S,S)-[-CH(Ph)NHCO(2-PPh₂-C₆H₄)]2; Pd(dba)3*CHCl₃ / CH₂Cl₂ / 20 h / 20 °C

4.1: 96 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

5.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 5 h / 0 °C

6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

6.2: tetrahydrofuran / 3 h / -107 °C

With n-butyllithium; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; silver(l) oxide; tris(dibenzylideneacetone)dipalladium chloroform complex; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 3.1: Mitsunobu reaction / 6.1: Cram reaction;

DOI:10.1021/ja011424b

Reference yield:

(S)-3-tert-butyldimethylsilyloxy-2-methylhex-4-yne-3-one (370561-80-1) → (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester (370562-13-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2-methyl (S)-CBS-oxazaborolidine; BH₃*SMe₂ / tetrahydrofuran / 1 h / -30 °C

2.1: 92 percent / Ag₂O / diethyl ether / 3.5 h / 20 °C

3.1: 85 percent / CpRu(CH₃CN)3PF₆ / acetone / 0.33 h / 20 °C

4.1: 51 percent / Bu₄NCl / (S,S)-[-CH(Ph)NHCO(2-PPh₂-C₆H₄)]2; Pd(dba)3*CHCl₃ / CH₂Cl₂ / 20 h / 20 °C

5.1: 96 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

6.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 5 h / 0 °C

7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

7.2: tetrahydrofuran / 3 h / -107 °C

With n-butyllithium; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; silver(l) oxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; tris(dibenzylideneacetone)dipalladium chloroform complex; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 4.1: Mitsunobu reaction / 7.1: Cram reaction;

DOI:10.1021/ja011424b

Reference yield:

(2S,3S)-tert-butyldimethylsilyloxy-2-methyl-3-methoxy-hex-4-yne (370561-82-3) → (E)-(2S,3S,4S,5R,9R)-3-Hydroxy-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienethioic acid S-tert-butyl ester (370562-13-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 85 percent / CpRu(CH₃CN)3PF₆ / acetone / 0.33 h / 20 °C

2.1: 51 percent / Bu₄NCl / (S,S)-[-CH(Ph)NHCO(2-PPh₂-C₆H₄)]2; Pd(dba)3*CHCl₃ / CH₂Cl₂ / 20 h / 20 °C

3.1: 96 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

4.1: 84 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 5 h / 0 °C

5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 3 h / -107 °C

With n-butyllithium; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; Dess-Martin periodane; diisopropylamine; tris(dibenzylideneacetone)dipalladium chloroform complex; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; (+)-1(S),2(S)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In tetrahydrofuran; dichloromethane; acetone; 2.1: Mitsunobu reaction / 5.1: Cram reaction;

DOI:10.1021/ja011424b

upstream raw materials:

tert-butyl thiopropionate

(E)-(2R,3R,7R)-3-Methoxy-7-(4-methoxy-phenoxy)-2,5-dimethyl-nona-4,8-dienal

(S)-3-tert-butyldimethylsilyloxy-2-methylhex-4-yne-3-one

(2S,3S)-tert-butyldimethylsilyloxy-2-methyl-3-methoxy-hex-4-yne

Downstream raw materials:

(E)-(2R,3S,4R,5R,9R)-3-(tert-butyldimethylsilanyloxy)-5-methoxy-9-(4-methoxyphenoxy)-2,4,7-trimethylundeca-6,10-dienethioic acid S-tert-butyl ester

(E)-(2S,3S,4R,5R,9R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-9-(4-methoxy-phenoxy)-2,4,7-trimethyl-undeca-6,10-dienal

(E)-(2S,3R,4S,5R,6R,10R)-6-[4-(tert-butyldimethylsilanyloxy)-2-hydroxy-6-methoxy-10-(4-methoxyphenoxy)-3,5,8-trimethyldodeca-7,11-dienyl]-2,2-dimethyl[1,3]dioxin-4-one

6-[(E)-(2S,3R,4S,5R,6R,10R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-10-(4-methoxy-phenoxy)-3,5,8-trimethyl-dodeca-7,11-dienyl]-2,2-dimethyl-[1,3]dioxin-4-one