(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

Base Information

Chemical Name:(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one
CAS No.:185300-94-1
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

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Technology Process of (R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

There total 1 articles about (R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-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: 87.0%

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 104486-82-0
(R)-3-((2S,3R)-3-Hydroxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

: 185300-94-1
(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; for 1h;
DOI:10.1021/jo961841k

Reference yield:

: 185300-94-1
(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

: (S)-3-[(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-acetyl]-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) H₂O, LiBH₄, 2.) aq. NaOH / 1.) Et₂O, THF, 0 deg C - 1 h, 23 deg C - 1 h, 2.) Et₂O, THF, 23 deg C, 1 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

3: 74 percent / TiCl₄ / CH₂Cl₂ / 16 h / -78 °C

4: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min

5: 1.) 4-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, toluene, 1.5 h, 2.) t-BuOH, THF, H₂O, toluene, 30 min

6: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

8: H₂ / Pd/C / methanol / 24 h / Ambient temperature

9: camphorsulfonic acid / methanol / 8 h

10: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; water; hydrogen; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo961841k

Reference yield:

: 185300-94-1
(R)-3-((2S,3R)-3-Benzyloxy-2-methyl-butyryl)-4-isopropyl-oxazolidin-2-one

: (S)-3-[(S)-2-(3,4-Dimethoxy-benzyloxy)-2-((2R,5S,6R)-2-methoxy-5,6-dimethyl-4-oxo-tetrahydro-pyran-2-yl)-acetyl]-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) H₂O, LiBH₄, 2.) aq. NaOH / 1.) Et₂O, THF, 0 deg C - 1 h, 23 deg C - 1 h, 2.) Et₂O, THF, 23 deg C, 1 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

3: 74 percent / TiCl₄ / CH₂Cl₂ / 16 h / -78 °C

4: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min

5: 1.) 4-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, toluene, 1.5 h, 2.) t-BuOH, THF, H₂O, toluene, 30 min

6: 1.) Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min, 2.) CH₂Cl₂, -78 deg C - 3 h, 0 deg C - 30 min

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

8: H₂ / Pd/C / methanol / 24 h / Ambient temperature

9: camphorsulfonic acid / methanol / 8 h

10: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, -78 deg C -> 0 deg C

With 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; water; hydrogen; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo961841k