<4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: <4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone
• CAS No.: 95481-54-2
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.353

Synonyms:<4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property of <4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

Chemical Property:

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Technology Process of <4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

There total 1 articles about <4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-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:

furfural (98-01-1) + C39H42BN3O9 → <4R-<4α(2R*,3R*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone (95481-54-2)

Guidance literature:

DOI:10.1016/S0040-4039(01)91392-9

Reference yield: 95.0%

<4R-<4α(2R*,3R*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone (95481-54-2) → (4R,5S)-3-[(R)-2-((R)-6-Hydroxy-3-oxo-3,6-dihydro-2H-pyran-2-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:

With water; bromine; In acetonitrile; at -20 ℃; for 1h;

DOI:10.1016/0040-4020(95)01107-2

Reference yield:

<4R-<4α(2R*,3R*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone (95481-54-2) → O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-4-O-(4-nitrobenzoate)-2,3,6-trideoxy-β-L-galacto-heptopyranoside (136113-81-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Br₂, H₂O / acetonitrile / 1 h / -20 °C

2: 51 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

3: 1.) copper iodide, 2.) chlorotrimethylsilane / 1.) Et₂O, THF, 0 deg C, 20 min, 2.) Et₂O, THF, -78 deg C, 30 min

4: 1.) NaBH₄, 2.) camphorsulfonic acid / 1.) EtOH, THF, -20 deg C, 1.5 h, 2.) EtOH, THF, -20 deg C, 15 min

5: 80 percent / DIBAL-H / hexane; tetrahydrofuran / 1 h / 0 °C

6: 73 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 22 h / Ambient temperature

7: 80 percent / diethylazodicarboxylate, Ph₃P / benzene / 20 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; copper(l) iodide; chloro-trimethyl-silane; camphor-10-sulfonic acid; water; bromine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; benzene;

DOI:10.1016/0040-4020(95)01107-2

upstream raw materials:

furfural

Downstream raw materials:

O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-4-O-(4-nitrobenzoate)-2,3,6-trideoxy-β-L-galacto-heptopyranoside

<4R,5S>-4'-methyl-5'-phenyl-2'-oxazolidinon-3'-yl-(O-tert-butyldimethylsilyl-2,6-dimethyl-2,3,6-trideoxy-β-L-xylo-hept-4-ulo-pyranosiduron)imide

<2α(2Z,4S,5R,6E,8S),3β,5α,6α>-4,6-dimethyl-1-tert-butyldiphenylsilyloxy-3-triisopropylsiloxy-8--2,6-octadiene

<4R,5S>-4'-methyl-5'-phenyl-2'-oxazolidinon-3'-yl-(O-tert-butyldimethylsilyl-6-methyl-2,3,6-trideoxy-β-L-threo-hept-2-en-4-ulo-pyranosiduron)imide

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