Acetic acid, [[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(2-propenyl)-1,3-dioxan-5-yl]oxy]-, 1,1-dimethylethyl ester

Base Information

Chemical Name:Acetic acid, [[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(2-propenyl)-1,3-dioxan-5-yl]oxy]-, 1,1-dimethylethyl ester
CAS No.:337309-17-8
Molecular Formula:C20H28O6
Molecular Weight:364.439
Hs Code.:

Synonyms:

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Chemical Property of Acetic acid, [[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(2-propenyl)-1,3-dioxan-5-yl]oxy]-, 1,1-dimethylethyl ester

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Technology Process of Acetic acid, [[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(2-propenyl)-1,3-dioxan-5-yl]oxy]-, 1,1-dimethylethyl ester

There total 1 articles about Acetic acid, [[(2R,4S,5R)-2-(4-methoxyphenyl)-4-(2-propenyl)-1,3-dioxan-5-yl]oxy]-, 1,1-dimethylethyl 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: 82.0%

: 5292-43-3
bromoacetic acid tert-butyl ester

: 220256-94-0
(2R,4S,5R)-4-allyl-2-(4-methoxyphenyl)-[1,3]dioxan-5-ol

: 337309-17-8
[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

: 337309-17-8
[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester

: 474125-29-6
(2R,4aR,6S,7R,9S,10aS)-7-Benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-9-methyl-octahydro-1,3,5-trioxa-benzocyclooctene

Guidance literature:: Multi-step reaction with 9 steps

1: 40 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

2: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / Heating

3: 98 percent / LiAlH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

4: 88 percent / NEt₃; DMAP / CH₂Cl₂ / 16 h / 20 °C

5: 79 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.5 h / -60 °C

6: 74 percent / diethyl ether / 0.5 h / -78 °C

7: 95 percent / TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C

8: 97 percent / NaBH(OAc)3; AcOH / acetonitrile / 2 h / -20 °C

9: NaH / tetrahydrofuran; dimethylformamide / 20 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5: Swern oxidation;
DOI:10.1039/b009506k

Reference yield:

: 337309-17-8
[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester

: 499237-58-0
((2R,3S,5S,7R,8S)-7-Benzyloxy-8-benzyloxymethyl-5-methyl-3-triethylsilanyloxy-oxocan-2-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 14 steps

1: 40 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

2: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / Heating

3: 98 percent / LiAlH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

4: 88 percent / NEt₃; DMAP / CH₂Cl₂ / 16 h / 20 °C

5: 79 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.5 h / -60 °C

6: 74 percent / diethyl ether / 0.5 h / -78 °C

7: 95 percent / TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C

8: 97 percent / NaBH(OAc)3; AcOH / acetonitrile / 2 h / -20 °C

9: NaH / tetrahydrofuran; dimethylformamide / 20 h / 0 - 20 °C

10: 68 percent / aq. TsOH / methanol / 24 h / 20 °C

11: 87 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 24 h / 0 - 20 °C

12: 78 percent / dimethylsulfoxide / 48 h / 40 °C

13: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -30 - -20 °C

14: DIBAL-H / CH₂Cl₂ / 1 h / -70 - -60 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; sodium tris(acetoxy)borohydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 5: Swern oxidation;
DOI:10.1039/b009506k