4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

Base Information

Chemical Name:4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose
CAS No.:217185-55-2
Molecular Formula:C₁₈H₁₉BrO₅
Molecular Weight:395.25
Hs Code.:

Synonyms:4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

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Chemical Property of 4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

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Technology Process of 4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

There total 6 articles about 4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-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: 72.0%

: 171076-03-2
methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

: 217185-55-2
4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

Guidance literature:: With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 3h; Heating;
DOI:10.1021/jo981225j

Reference yield:

: 131529-45-8
methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside

: 217185-55-2
4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) trifluoroacetic anhydride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂, 24 h

2: 1.) lithium 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

3: 56 percent / palladium(II) chloride, copper(II) chloride, oxygen / dimethylformamide; H₂O / Ambient temperature

4: 90 percent / potassium tert-butoxide / toluene / 0.5 h / Ambient temperature

5: 72 percent / barium carbonate, N-bromosuccinimide / CCl₄ / 3 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; potassium tert-butylate; oxygen; dimethyl sulfoxide; triethylamine; barium carbonate; trifluoroacetic anhydride; copper dichloride; palladium dichloride; lithium hexamethyldisilazane; In tetrachloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981225j

Reference yield:

: 135700-48-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

: 217185-55-2
4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) lithium 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

2: 56 percent / palladium(II) chloride, copper(II) chloride, oxygen / dimethylformamide; H₂O / Ambient temperature

3: 90 percent / potassium tert-butoxide / toluene / 0.5 h / Ambient temperature

4: 72 percent / barium carbonate, N-bromosuccinimide / CCl₄ / 3 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; potassium tert-butylate; oxygen; barium carbonate; copper dichloride; palladium dichloride; lithium hexamethyldisilazane; In tetrachloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981225j