methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose
CAS No.:217185-54-1
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

There total 4 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose 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:

: 126108-10-9
methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside

: 217185-54-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) trifluoroacetic anhydride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂

2: 56 percent / triethylamine / dimethylformamide / 48 h

3: 1.) sodium hexamethyldisilazide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 0 deg C, 1 h, 2.) THF, room temperature, 24 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In N,N-dimethyl-formamide;
DOI:10.1021/jo981225j

Reference yield:

: 135759-86-3
methyl 4,6-O-benzylidene-2-deoxy-2-C-propenyl-α-D-arabino-hexopyranosid-3-ulose

: 217185-54-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / triethylamine / dimethylformamide / 48 h

2: 1.) sodium hexamethyldisilazide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 0 deg C, 1 h, 2.) THF, room temperature, 24 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hexamethyldisilazane; triethylamine; In N,N-dimethyl-formamide;
DOI:10.1021/jo981225j

Reference yield:

: 66537-92-6
methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside

: 217185-54-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-2-C-propenyl-α-D-erythro-hexopyranosid-3-ulose

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / tetrahydrofuran / 2 h / Heating

2: 1.) trifluoroacetic anhydride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂

3: 56 percent / triethylamine / dimethylformamide / 48 h

4: 1.) sodium hexamethyldisilazide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 0 deg C, 1 h, 2.) THF, room temperature, 24 h

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo981225j