(E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one

Base Information

• Chemical Name: (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one
• CAS No.: 753016-44-3
• Molecular Formula: C₄₅H₅₈O₆Si
• Molecular Weight: 723.037
• Mol file: 753016-44-3.mol

Synonyms:(E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one

Chemical Property of (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one

There total 17 articles about (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-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: 80.0%

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-enal (753016-41-0) + (S)-1-(tert-butyldiphenylsiloxy)-2-(4-methoxybenzyloxymethyl)-3-pentanone (680201-67-6) → (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one (753016-44-3)

Guidance literature:

With tin(II) trifluoromethanesulfonate; triethylamine;

DOI:10.1016/j.tetlet.2005.07.029

Reference yield:

(E)-(3'-bromo-but-2'-enyloxymethyl)-benzene (157733-27-2) → (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one (753016-44-3)

Guidance literature:

Multi-step reaction with 4 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

With tin(II) trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; hexane; dichloromethane; 4.2: Paterson's stereoselective aldol reaction;

DOI:10.1021/ol049219z

Reference yield:

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-en-1-ol (753016-63-6) → (E)-(2S,4S,5R,6S)-10-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-(4-methoxy-benzyloxymethyl)-4,6,8-trimethyl-dec-8-en-3-one (753016-44-3)

Guidance literature:

Multi-step reaction with 2 steps

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

With tin(II) trifluoromethanesulfonate; triethylamine; 1: Swern oxidation;

DOI:10.1016/j.tetlet.2005.07.029

upstream raw materials:

(E)-(S)-6-Benzyloxy-2,4-dimethyl-hex-4-enal

(S)-1-(tert-butyldiphenylsiloxy)-2-(4-methoxybenzyloxymethyl)-3-pentanone

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

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

Downstream raw materials:

(-)-kazusamycin A

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

(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

((E)-(1R,2S)-6-Benzyloxy-1-{(R)-1-[(4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-2,4-dimethyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane