1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

Base Information

Chemical Name:1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol
CAS No.:89873-08-5
Molecular Formula:C₁₇H₂₀O₅
Molecular Weight:304.343
Hs Code.:

Synonyms:1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

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Chemical Property of 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

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Technology Process of 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

There total 10 articles about 1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol 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: 90.0%

: 89873-07-4
1,5-Anhydro-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

: 89873-08-5
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h;
DOI:10.1021/jo00187a010

Reference yield:

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

: 89873-08-5
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

Guidance literature:: Multi-step reaction with 10 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: 90 percent / Dimethylsulfoxide, Trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

6: 80 percent / acetonitrile / Heating

7: 90 percent / Diisobutylaluminum hydride / toluene / 1 h / 0 °C

8: Mercuric trifluoroacetate

9: 85 percent / benzonitrile / 1 h / Heating

10: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h

With 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; mercury(II) trifluoroacetate; diisobutylaluminium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; zinc(II) chloride; nickel; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; benzonitrile; toluene; acetonitrile;
DOI:10.1021/jo00187a010

Reference yield:

: 89872-96-8
1,5-Anhydro-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-D-glucitol

: 89873-08-5
1,5-Anhydro-4,6-O-benzylidene-3-deoxy-3-C-(formylmethyl)-3-C-vinyl-D-allitol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / Dimethylsulfoxide, Trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

2: 80 percent / acetonitrile / Heating

3: 90 percent / Diisobutylaluminum hydride / toluene / 1 h / 0 °C

4: Mercuric trifluoroacetate

5: 85 percent / benzonitrile / 1 h / Heating

6: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.5 h

With tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; benzonitrile; toluene; acetonitrile;
DOI:10.1021/jo00187a010