(E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester
• CAS No.: 860160-10-7
• Molecular Formula: C₃₅H₅₈O₆Si
• Molecular Weight: 602.927
• Mol file: 860160-10-7.mol

Synonyms:(E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester

Chemical Property of (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester

There total 24 articles about (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl 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:

(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene (157733-27-2) → (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester (860160-10-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 68 percent / PdCl₂[P(o-Tol)3]2 / tetrahydrofuran / 96 h / 20 °C

2.1: 96 percent / DIBAL / CH₂Cl₂; hexane / -78 - 45 °C

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

4.1: Sn(OTf)2; Et₃N / CH₂Cl₂ / 3 h / -78 °C

4.2: 77 percent / CH₂Cl₂ / 6 h / -78 °C

5.1: diethylmethoxyborane / tetrahydrofuran; methanol / 0.25 h / 20 °C

5.2: 73 percent / NaBH₄ / tetrahydrofuran; methanol / 48 h / -78 °C

6.1: 92 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 86 percent / PPTS / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

9.1: 68 percent / DDQ / CH₂Cl₂; aq. phosphate buffer / 6 h / 0 °C / pH 7

10.1: 67.4 mg / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

11.1: 49.8 mg / toluene / 2 h / Heating

With 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; toluene; 4.2: Paterson's stereoselective aldol reaction / 11.1: Wittig olefination;

DOI:10.1021/ol049219z

Reference yield:

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-en-1-ol (753016-63-6) → (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester (860160-10-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / Sn(OTf)2; triethylamine

2: Et₂BOMe; NaBH₄

3: TBAF / tetrahydrofuran

4: PPTS

5: 2,6-lutidine

6: 65 percent / DDQ

7: toluene

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; toluene; 1: Swern oxidation / 8: Swern oxidation / 9: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.029

Reference yield:

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-enal (753016-41-0) → (E)-3-{(4S,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxan-5-yl}-2-methyl-acrylic acid ethyl ester (860160-10-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / Sn(OTf)2; triethylamine

2: Et₂BOMe; NaBH₄

3: TBAF / tetrahydrofuran

4: PPTS

5: 2,6-lutidine

6: 65 percent / DDQ

7: toluene

With 2,6-dimethylpyridine; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; diethyl methoxy borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; toluene; 7: Swern oxidation / 8: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.029

upstream raw materials:

(carbethoxyethylidene)triphenylphosphorane

(4R,5S)-4-[(E)-(1R,2R,3S)-7-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1,3,5-trimethyl-hept-5-enyl]-2,2-dimethyl-[1,3]dioxane-5-carbaldehyde

2-hydroxymethyl-1-(4-methoxybenzyloxy)-3-pentanone

(R)-2-hydroxymethyl-1-(4-methoxybenzyloxy)-3-pentanone

Downstream raw materials:

(-)-kazusamycin A