methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

Base Information

Chemical Name:methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate
CAS No.:146608-29-9
Molecular Formula:C₂₂H₂₈Br₂O₅
Molecular Weight:532.269
Hs Code.:

Synonyms:methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

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Chemical Property of methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

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Technology Process of methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

There total 22 articles about methyl (E)-(4S,5S,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate 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: 85.0%

: 558-13-4
carbon tetrabromide

: 146517-99-9
(E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester

: 120040-82-6,146608-29-9
methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

Guidance literature:: With 4 A molecular sieve; triphenylphosphine; In dichloromethane; for 0.5h;
DOI:10.1021/ja00059a024

Reference yield:

: 120143-05-7
(3S,4S,5S)-4-(benzyloxy)-5,6-(isopropylidenedioxy)-3-methylhex-1-ene

: 120040-82-6,146608-29-9
methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -78 deg C, 30 min, 2.) MeOH, RT

2: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

3: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

4: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

5: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

6: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

7: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

8: 85 percent / 4 Angstroem molecular sieves, Ph₃P / CH₂Cl₂ / 0.5 h

With dmap; sodium tetrahydroborate; sodium periodate; dimethylsulfide; 4 A molecular sieve; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00059a024

Reference yield:

: 120040-77-9
(2R,3S)-3-Benzyloxy-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde

: 120040-82-6,146608-29-9
methyl (E)-(4S,5R,6S,7S)-5-acetoxy-7-(benzyloxy)-9,9-dibromo-2,4,6-trimethylnona-2,8-dienoate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 4 Angstroem molecular sieves, 3.) NaBH₄

2: 1.) O₃, 2.) Ph₃P / 1.) MeOH, -78 deg C, 2.) MeOH, RT, 2 h

3: 88 percent / toluene; CH₂Cl₂ / 12 h / 45 °C

4: 95 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h

5: 98 percent / aq. AcOH / methanol / 25 h / 95 °C

6: NaIO₄ / tetrahydrofuran; H₂O / 4 h / 25 °C

7: 85 percent / 4 Angstroem molecular sieves, Ph₃P / CH₂Cl₂ / 0.5 h

With dmap; sodium tetrahydroborate; sodium periodate; 4 A molecular sieve; ozone; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00059a024