5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

Base Information

• Chemical Name: 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone
• CAS No.: 688329-96-6
• Molecular Formula: C₃₈H₆₄O₅Si
• Molecular Weight: 629.009
• Mol file: 688329-96-6.mol

Synonyms:5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

Chemical Property of 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

There total 12 articles about 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone 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:

Oleic aldehyde (2423-10-1) → 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

1.2: 74 percent / hexamethylphosphoramide / tetrahydrofuran / 2 h / -78 - -40 °C

2.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

3.1: 0.20 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / CH₂Cl₂ / 6 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-96-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 14 h / 20 °C

2.1: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

3.1: 95 percent / AIBN; tributyltin hydride / toluene / 1 h / 90 °C

4.1: 95 percent / acetic acid; H₂ / palladium on carbon / ethyl acetate / 6 h

5.1: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

6.2: 74 percent / hexamethylphosphoramide / tetrahydrofuran / 2 h / -78 - -40 °C

7.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

8.1: 0.20 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3.1: Barton deoxygenation;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

C18H22O6 (188682-04-4) → 5-O-tert-butyldimethylsilyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-96-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Dowex H¹⁺ resin / tetrahydrofuran; H₂O / 24 h / Heating

2.1: sodium periodate / methanol; H₂O / 1 h / 20 °C

3.1: 5 g / sodium borohydride / methanol / 0 °C

4.1: 84 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 14 h / 20 °C

5.1: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

6.1: 95 percent / AIBN; tributyltin hydride / toluene / 1 h / 90 °C

7.1: 95 percent / acetic acid; H₂ / palladium on carbon / ethyl acetate / 6 h

8.1: 90 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

9.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

9.2: 74 percent / hexamethylphosphoramide / tetrahydrofuran / 2 h / -78 - -40 °C

10.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

11.1: 0.20 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); Dowex H¹⁺ resin; hydrogen; tri-n-butyl-tin hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; 6.1: Barton deoxygenation;

DOI:10.1016/j.ejmech.2003.10.006

upstream raw materials:

Oleic aldehyde

tert-butyldimethylsilyl chloride

C₁₈H₂₂O₆

5-O-tert-butyldimethylsilyl-4-C-(2-hydroxyethyl)-2,3-dideoxy-D-glycero-pentono-1,4-lactone

Downstream raw materials:

5-O-acetyl-4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone

4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(Z)-9-octadecaenylidene]-2,3-dideoxy-D-glycero-pentono-1,4-lactone