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

Base Information

• Chemical Name: 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone
• CAS No.: 688329-90-0
• Molecular Formula: C₂₀H₃₂O₄Si
• Molecular Weight: 364.557
• Mol file: 688329-90-0.mol

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

Chemical Property of 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-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 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone

There total 7 articles about 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-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: 95.0%

thiocarbonic acid O-{2-benzyloxy-1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-2-yl]-ethyl} ester O-phenyl ester → 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-90-0)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 1h;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 14 h / 20 °C

2: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

3: 95 percent / AIBN; tributyltin hydride / toluene / 1 h / 90 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; toluene; 3: Barton deoxygenation;

DOI:10.1016/j.ejmech.2003.10.006

Reference yield:

C18H22O6 (188682-04-4) → 4-C-(2-benzyloxyethyl)-5-O-tert-butyldimethylsilyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone (688329-90-0)

Guidance literature:

Multi-step reaction with 6 steps

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

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

3: 5 g / sodium borohydride / methanol / 0 °C

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

5: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / 20 °C

6: 95 percent / AIBN; tributyltin hydride / toluene / 1 h / 90 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; 2,2'-azobis(isobutyronitrile); Dowex H¹⁺ resin; tri-n-butyl-tin hydride; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 6: Barton deoxygenation;

DOI:10.1016/j.ejmech.2003.10.006

upstream raw materials:

tert-butyldimethylsilyl chloride

C₁₈H₂₂O₆

6-O-benzyl-4-C-hydroxymethyl-2,3-dideoxy-D-threo-hexono-1,4-lactone

Downstream raw materials:

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

4-C-(2-benzyloxyethyl)-5-O-tetradecanoyl-2,3-dideoxy-D-glycero-pentono-1,4-lactone

4-C-(2-(4-methoxyphenoxy)ethyl)-2-C-[(E)-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