(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

Base Information

Chemical Name:(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one
CAS No.:260449-38-5
Molecular Formula:C₂₄H₃₈O₃Si
Molecular Weight:402.649
Hs Code.:

Synonyms:(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

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Chemical Property of (E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

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Technology Process of (E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

There total 12 articles about (E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-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:

: 22089-60-7
benzyl prenyl ether

: 260449-38-5
(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

Guidance literature:: Multi-step reaction with 13 steps

1: 58 percent / SeO₂; TBHP / CH₂Cl₂ / 8 h / 25 °C

2: 94 percent / diethyl ether / 0.5 h / 0 - 5 °C

3: 43 percent / Ti(iPrO)4; (+)-DIPT; TBHP / toluene; CH₂Cl₂ / 0.42 h / 20 °C

4: 80 percent / Cp₂TiCl₂; cyclohexa-1,4-diene; ZnCl₂ / Zn / tetrahydrofuran / 8 h / -15 - 25 °C

5: H₂ / Pd/C / methanol / 0.5 h / 25 °C

6: CSA / acetone / 1 h / 0 °C

7: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

8: diethyl ether / 0.5 h / 0 °C

9: PTSA / methanol / 0.5 h / 25 °C

10: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11: CSA / methanol; CH₂Cl₂ / 0.5 h / 0 - 10 °C

12: (COCl)2; DMSO; Et₃M / CH₂Cl₂ / 1.5 h / -78 - 0 °C

13: nBuLi / tetrahydrofuran / 3 h / -78 - 25 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; n-butyllithium; selenium(IV) oxide; oxalyl dichloride; L-(+)-diisopropyl tartrate; cyclohexa-1,4-diene; camphor-10-sulfonic acid; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; zinc(II) chloride; palladium on activated charcoal; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; 1: Oxidation / 2: Methylation / 3: Epoxidation / 4: Ring cleavage / 5: Hydrogenolysis / 6: Etherification / 7: Oxidation / 8: Wittig methylenation / 9: deprotection / 10: Etherification / 11: deprotection / 12: Swern oxidation / 13: Horner-Wadsworth-Emmons olefination;
DOI:10.1246/cl.2000.80

Reference yield:

: 101376-74-3
(E)-4-(benzyloxy)-2-methylbut-2-enal

: 260449-38-5
(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

Guidance literature:: Multi-step reaction with 12 steps

1: 94 percent / diethyl ether / 0.5 h / 0 - 5 °C

2: 43 percent / Ti(iPrO)4; (+)-DIPT; TBHP / toluene; CH₂Cl₂ / 0.42 h / 20 °C

3: 80 percent / Cp₂TiCl₂; cyclohexa-1,4-diene; ZnCl₂ / Zn / tetrahydrofuran / 8 h / -15 - 25 °C

4: H₂ / Pd/C / methanol / 0.5 h / 25 °C

5: CSA / acetone / 1 h / 0 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

7: diethyl ether / 0.5 h / 0 °C

8: PTSA / methanol / 0.5 h / 25 °C

9: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10: CSA / methanol; CH₂Cl₂ / 0.5 h / 0 - 10 °C

11: (COCl)2; DMSO; Et₃M / CH₂Cl₂ / 1.5 h / -78 - 0 °C

12: nBuLi / tetrahydrofuran / 3 h / -78 - 25 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; n-butyllithium; oxalyl dichloride; L-(+)-diisopropyl tartrate; cyclohexa-1,4-diene; camphor-10-sulfonic acid; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; zinc(II) chloride; palladium on activated charcoal; zinc; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; 1: Methylation / 2: Epoxidation / 3: Ring cleavage / 4: Hydrogenolysis / 5: Etherification / 6: Oxidation / 7: Wittig methylenation / 8: deprotection / 9: Etherification / 10: deprotection / 11: Swern oxidation / 12: Horner-Wadsworth-Emmons olefination;
DOI:10.1246/cl.2000.80

Reference yield:

: 191410-59-0
(2R,3R,4S)-1-benzyloxy-3-methyl-2,4-pentanediol

: 260449-38-5
(E)-(6S,7R)-1-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethyl-nona-4,8-dien-3-one

Guidance literature:: Multi-step reaction with 9 steps

1: H₂ / Pd/C / methanol / 0.5 h / 25 °C

2: CSA / acetone / 1 h / 0 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4: diethyl ether / 0.5 h / 0 °C

5: PTSA / methanol / 0.5 h / 25 °C

6: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: CSA / methanol; CH₂Cl₂ / 0.5 h / 0 - 10 °C

8: (COCl)2; DMSO; Et₃M / CH₂Cl₂ / 1.5 h / -78 - 0 °C

9: nBuLi / tetrahydrofuran / 3 h / -78 - 25 °C

With 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; 1: Hydrogenolysis / 2: Etherification / 3: Oxidation / 4: Wittig methylenation / 5: deprotection / 6: Etherification / 7: deprotection / 8: Swern oxidation / 9: Horner-Wadsworth-Emmons olefination;
DOI:10.1246/cl.2000.80