(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Base Information

Chemical Name:(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:264920-92-5
Molecular Formula:C₂₇H₃₃NO₆
Molecular Weight:467.562
Hs Code.:

Synonyms:(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Chemical Property of (4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

There total 1 articles about (4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one 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: 68.0%

: 77877-20-4
(4R,5S)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

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

: 264920-92-5
(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -78 ℃; for 6h;
DOI:10.1021/ol005510c

Reference yield: 80.0%

: 124-41-4
sodium methylate

: 264920-92-5
(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

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

Guidance literature:: With methanol; at -78 - -10 ℃; for 2h;
DOI:10.1021/ol005510c

Reference yield:

: 264920-92-5
(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

: 264921-00-8
(2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / MeOH / 2 h / -78 - -10 °C

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

3: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

4: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

5: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

6: 86 percent / p-TsOH / tetrahydrofuran; H₂O / 25 °C

7: Et₃N; DMAP / CH₂Cl₂ / 2 h / 22 °C

8: 95 percent / BF₃*OEt₂ / diethyl ether / -78 °C

With 2,6-dimethylpyridine; methanol; dmap; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1: methanolysis / 2: silylation / 3: Reduction / 4: Swern oxidation / 5: Wittig reaction / 6: Cyclization / 7: Acetylation / 8: allylation;
DOI:10.1021/ol005510c