1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

Base Information

Chemical Name:1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol
CAS No.:89889-00-9
Molecular Formula:C₂₁H₃₂O₅Si
Molecular Weight:392.568
Hs Code.:

Synonyms:1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

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Chemical Property of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

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Technology Process of 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

There total 7 articles about 1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol 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: 89.0%

: 89872-99-1
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((E)-carbethoxymethylene)-2-deoxy-D-arabino-2-hexitol

: 89889-00-9
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at 0 ℃; for 0.5h;
DOI:10.1021/jo00187a010

Reference yield:

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

: 89889-00-9
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

Guidance literature:: Multi-step reaction with 7 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

6: 80 percent / acetonitrile / Heating

7: 89 percent / Diisobutylaluminum hydride / toluene / 0.5 h / 0 °C

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

Reference yield:

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

: 89889-00-9
1,5-Anhydro-4,6-O-benzylidene-3-O-(tert-butyldimethylsilyl)-2-C-((hydroxymethyl)methylene)-2-deoxy-D-arabino-hexitol

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / Dimethylsulfoxide, Trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / -78 °C

2: 80 percent / acetonitrile / Heating

3: 89 percent / Diisobutylaluminum hydride / toluene / 0.5 h / 0 °C

With diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic anhydride; In dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00187a010