(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

Base Information

Chemical Name:(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone
CAS No.:647007-87-2
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

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Chemical Property of (4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

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Technology Process of (4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

There total 1 articles about (4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone 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: 81.4%

: 78-84-2
isobutyraldehyde

: 212712-42-0
(+)-(S)-4′′-benzyl-3′′-(3-(3′,4′-methylenedioxyphenyl)propanoyl)oxazolidin-2′′-one

: 647007-87-2
(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

Guidance literature:: (+)-(S)-4′′-benzyl-3′′-(3-(3′,4′-methylenedioxyphenyl)propanoyl)oxazolidin-2′′-one; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 - 0 ℃;

isobutyraldehyde; In dichloromethane; at -78 - -15 ℃;
DOI:10.1271/bbb.67.2215

Reference yield:

: 647007-87-2
(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

: (2S,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-hydroxy-3-isopropyl-5-(4-methoxy-phenyl)-pent-4-ynal

Guidance literature:: Multi-step reaction with 6 steps

1: 91.2 percent / lithium borohydride / diethyl ether; H₂O / 0 - 20 °C

2: 98.3 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 0 - 20 °C

3: 90.8 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4: 79.7 percent / acetic acid / tetrahydrofuran; H₂O / 16 h / 20 °C

5: tetrahydrofuran / -78 °C

6: N-methylmorpholine N-oxide; molecular sieves 4 Angstroem; tetrapropylammonium perruthenate / CH₂Cl₂ / 12 h / 20 °C

With 1H-imidazole; dmap; lithium borohydride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1271/bbb.67.2215

Reference yield:

: 647007-87-2
(4S)-4-benzyl-1-[(2S,3R)-3-hydroxy-4-methyl-2-(3,4-methylenedioxybenzyl)valeryl]-2-oxazolidinone

: 647008-05-7
(2R,3S)-5-(4-methoxyphenyl)-2-(3,4-methylenedioxybenzyl)-3-(1-methylethyl)-4-pentyne-1,3-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 91.2 percent / lithium borohydride / diethyl ether; H₂O / 0 - 20 °C

2: 98.3 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 0 - 20 °C

3: 90.8 percent / dimethyl sulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4: 79.7 percent / acetic acid / tetrahydrofuran; H₂O / 16 h / 20 °C

5: tetrahydrofuran / -78 °C

With 1H-imidazole; dmap; lithium borohydride; oxalyl dichloride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1271/bbb.67.2215