2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

Base Information

Chemical Name:2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol
CAS No.:157794-06-4
Molecular Formula:C₃₆H₄₈O₅Si
Molecular Weight:588.86
Hs Code.:

Synonyms:2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

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Chemical Property of 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

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Technology Process of 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

There total 7 articles about 2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 157903-84-9
3-(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1-propene

: 157794-06-4
2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo005593a

Reference yield:

: 58341-62-1
methyl 2-O-allyl-3-O-benzyl-α-D-glucopyranoside

: 157794-06-4
2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 2.) THF, DMF, 0 deg C to room t.

2: TMSOTf / acetonitrile / Ambient temperature

3: 65 percent / (Ph₃P)4RhH, TFA / ethanol / 0.75 h / Heating

4: 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; hydridotetakis(triphenylphosphine)rhodium(I); trimethylsilyl trifluoromethanesulfonate; sodium hydride; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)73310-7

Reference yield:

: 58341-63-2
methyl 2-O-allyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside

: 157794-06-4
2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

Guidance literature:: Multi-step reaction with 3 steps

1: TMSOTf / acetonitrile / Ambient temperature

2: 65 percent / (Ph₃P)4RhH, TFA / ethanol / 0.75 h / Heating

3: 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; hydridotetakis(triphenylphosphine)rhodium(I); trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)73310-7