Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

Base Information

Chemical Name:Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester
CAS No.:264920-99-2
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

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Chemical Property of Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

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Technology Process of Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

There total 8 articles about Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl 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:

: 108-24-7
acetic anhydride

: 264920-98-1
(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-ol

: 264920-99-2
Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 22 ℃; for 2h;
DOI:10.1021/ol005510c

Reference yield:

: 110597-90-5
(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal

: 264920-99-2
Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 68 percent / Bu₂BOTf; i-Pr₂NEt / diethyl ether / 6 h / -78 °C

2: 80 percent / MeOH / 2 h / -78 - -10 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

4: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

5: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

6: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

7: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

8: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

With 2,6-dimethylpyridine; methanol; dmap; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1: Heathcock anti-aldol reaction / 2: methanolysis / 3: silylation / 4: Reduction / 5: Swern oxidation / 6: Wittig reaction / 7: Cyclization / 8: Acetylation;
DOI:10.1021/ol005510c

Reference yield:

: 264920-93-6
(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester

: 264920-99-2
Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

2: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

3: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

4: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

5: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

6: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: silylation / 2: Reduction / 3: Swern oxidation / 4: Wittig reaction / 5: Cyclization / 6: Acetylation;
DOI:10.1021/ol005510c