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

Base Information

Chemical Name:(E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester
CAS No.:146517-99-9
Molecular Formula:C₂₁H₂₈O₆
Molecular Weight:376.45
Hs Code.:

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

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Chemical Property of (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester

Chemical Property:

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Technology Process of (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester

There total 8 articles about (E)-(4R,5S,6S,7S)-5-Acetoxy-7-benzyloxy-2,4,6-trimethyl-8-oxo-oct-2-enoic acid methyl ester 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:

: 146517-98-8
methyl (E)-(4S,5R,6S,7S,8S)-5-acetoxy-7-(benzyloxy)-8,9-dihydroxy-2,4,6-trimethylnon-2-enoate

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

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 25 ℃; for 4h;
DOI:10.1021/ja00059a024

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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

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

Guidance literature:: Multi-step reaction with 6 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

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