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
Hs Code.:

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

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

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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

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

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:

: 18162-48-6
tert-butyldimethylsilyl chloride

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

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:

: 188682-04-4
C₁₈H₂₂O₆

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

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