methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

Base Information

Chemical Name:methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate
CAS No.:359642-17-4
Molecular Formula:C₂₁H₂₇BrO₇
Molecular Weight:471.345
Hs Code.:

Synonyms:methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

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Chemical Property of methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

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Technology Process of methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

There total 5 articles about methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate 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%

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 359642-13-0
Acetic acid (1S,2S)-2-benzyloxy-1-bromomethyl-2-((4S,5R)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester

: 359642-17-4
methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

Guidance literature:: In toluene; at 20 ℃; for 24h;
DOI:10.1016/S0008-6215(01)00116-1

Reference yield:

: 149557-49-3
4-O-benzyl-2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal

: 359642-17-4
methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

Guidance literature:: Multi-step reaction with 5 steps

1: 70 percent / AcOH / H₂O / 20 °C

2: 61 percent / PPh₃; CBr₄ / tetrahydrofuran / 0.75 h / 20 °C

3: 51 percent / pyridine / 20 °C

4: 63 percent / HgO; HgCl₂ / acetone; H₂O / Heating

5: 72 percent / toluene / 24 h / 20 °C

With pyridine; carbon tetrabromide; acetic acid; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; water; acetone; toluene;
DOI:10.1016/S0008-6215(01)00116-1

Reference yield:

: 359642-14-1
4-O-benzyl-2,3-O-isopropylidene-D-glucose diethyl dithioacetal

: 359642-17-4
methyl 7-O-acetyl-4-O-benzyl-8-bromo-2,3,8-trideoxy-4,5-O-isopropylidene-D-gluco-oct-2-enonate

Guidance literature:: Multi-step reaction with 4 steps

1: 61 percent / PPh₃; CBr₄ / tetrahydrofuran / 0.75 h / 20 °C

2: 51 percent / pyridine / 20 °C

3: 63 percent / HgO; HgCl₂ / acetone; H₂O / Heating

4: 72 percent / toluene / 24 h / 20 °C

With pyridine; carbon tetrabromide; triphenylphosphine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; water; acetone; toluene;
DOI:10.1016/S0008-6215(01)00116-1