(4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate

Base Information

• Chemical Name: (4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate
• CAS No.: 382596-27-2
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.551
• DSSTox Substance ID: DTXSID50455248
• Wikidata: Q82277164
• Mol file: 382596-27-2.mol

Synonyms:382596-27-2;(4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate;3-O-tert-butyl 5-O-ethyl (4S,5R)-2,2-dimethyl-4-(4-phenylmethoxyphenyl)-1,3-oxazolidine-3,5-dicarboxylate;DTXSID50455248;MolPort-035-677-701;VGHPGNKDXWAOLE-FCHUYYIVSA-N;AKOS022175166;A924311;(4S,5R)-2,2-Dimethyl-4-[4-(phenylmethoxy)phenyl]-N-Dimethylethoxycarbonyl-3,5-oxazolidinecarboxylic;(4S,5R)-3-tert-Butyl5-ethyl4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate

Chemical Property of (4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate

Chemical Property:

• Boiling Point: 547.6±50.0 °C(Predicted)
• PKA: -3.42±0.70(Predicted)
• Density: 1.140±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 455.23078777
• Heavy Atom Count: 33
• Complexity: 658

Purity/Quality:

97% ^*data from raw suppliers

(4S,5R)-2,2-Dimethyl-4-[4-(phenylmethoxy)phenyl]-N-Dimethylethoxycarbonyl-3,5-oxazolidinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(N(C(O1)(C)C)C(=O)OC(C)(C)C)C2=CC=C(C=C2)OCC3=CC=CC=C3
• Isomeric SMILES: CCOC(=O)[C@H]1[C@@H](N(C(O1)(C)C)C(=O)OC(C)(C)C)C2=CC=C(C=C2)OCC3=CC=CC=C3
• Uses: (4S,5R)-2,2-DiMethyl-4-[4-(phenylMethoxy)phenyl]-N-DiMethylethoxycarbonyl-3,5-oxazolidinecarboxylic Acid Ethyl Ester is used in the synthesis of Paclitaxel metabolite.

Technology Process of (4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate

There total 5 articles about (4S,5R)-3-tert-Butyl 5-ethyl 4-(4-(benzyloxy)phenyl)-2,2-dimethyloxazolidine-3,5-dicarboxylate 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: 75.0%

2,2-dimethoxy-propane (77-76-9) + ethyl (2R,3S)-3-(tert-butoxycarbonylamino)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoate (382596-26-1) → ethyl (4S,5R)-4-[4-(benzyloxy)phenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate (382596-27-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene; at 90 ℃; for 8h;

DOI:10.1021/jo0102516

Reference yield:

p-benzyloxybenzaldehyde (4397-53-9) → ethyl (4S,5R)-4-[4-(benzyloxy)phenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate (382596-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / CH₂Cl₂ / 24 h / 20 °C

2.1: K₂[OsO₂(OH)4]; LiOH*H₂O; (DHQ)2PHAL / 2-methyl-propan-2-ol; H₂O; acetonitrile / 24 h / 0 - 5 °C

2.2: HCl / ethanol / 4 h / 90 °C

3.1: 23 g / NaHCO₃ / tetrahydrofuran / 5 h / 20 °C

4.1: 75 percent / PPTS / toluene / 8 h / 90 °C

With lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K2; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 1.1: Wittig olefination / 2.1: Sharpless aminohydroxylation;

DOI:10.1021/jo0102516

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → ethyl (4S,5R)-4-[4-(benzyloxy)phenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate (382596-27-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 23 g / NaHCO₃ / tetrahydrofuran / 5 h / 20 °C

2: 75 percent / PPTS / toluene / 8 h / 90 °C

With pyridinium p-toluenesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; toluene;

DOI:10.1021/jo0102516

upstream raw materials:

2,2-dimethoxy-propane

ethyl (2R,3S)-3-(tert-butoxycarbonylamino)-3-[4-(benzyloxy)phenyl]-2-hydroxypropanoate

p-benzyloxybenzaldehyde

di-tert-butyl dicarbonate

Downstream raw materials:

(4S,5R)-4-[4-(benzyloxy)phenyl]-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylic acid

7-benzyloxycarbonyl-3'-(4-benzyloxyphenyl)-3'-dephenylpaclitaxel

7-benzyloxycarbonylbaccatin III 13-O-[(4S,5R)-4-{4-(benzyloxy)phenyl}-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate]

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