1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

Base Information

Chemical Name:1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol
CAS No.:89872-98-0
Molecular Formula:C₁₉H₂₈O₅Si
Molecular Weight:364.514
Hs Code.:

Synonyms:1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

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Chemical Property of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

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Technology Process of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

There total 6 articles about 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol 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: 93.0%

: 89872-97-9
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-glucitol

: 89872-98-0
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

Guidance literature:: With dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo00187a010

Reference yield:

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 89872-98-0
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / H₂, Triethylamine / Raney nickel / ethyl acetate / 2 h / 50 °C / 51714.8 Torr

2: Triethylamine / methanol; H₂O / 10 h

3: ZnCl₂

4: 1.)Di-n-butyltin oxide, 2.)imidazole / 1.)Toluene, reflux, 4h, 2.)DMF, 70 deg C, 3 h

5: 93 percent / Dimethylsulfoxide, Trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; hydrogen; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; zinc(II) chloride; nickel; In methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo00187a010

Reference yield:

: 100-52-7
benzaldehyde

: 89872-98-0
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-D-arabino-2-ulohexitol

Guidance literature:: Multi-step reaction with 3 steps

1: ZnCl₂

2: 1.)Di-n-butyltin oxide, 2.)imidazole / 1.)Toluene, reflux, 4h, 2.)DMF, 70 deg C, 3 h

3: 93 percent / Dimethylsulfoxide, Trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; di(n-butyl)tin oxide; dimethyl sulfoxide; trifluoroacetic anhydride; zinc(II) chloride; In dichloromethane;
DOI:10.1021/jo00187a010