(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate

Base Information

• Chemical Name: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate
• CAS No.: 670254-71-4
• Molecular Formula: C23H27NO6
• Molecular Weight: 413.47
• Mol file: 670254-71-4.mol

Synonyms:

Chemical Property of (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate

Chemical Property:

• Melting Point: 100-102 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 527.1±50.0 °C(Predicted)
• PKA: -4.51±0.70(Predicted)
• PSA: 74.30000
• Density: 1.188±0.06 g/cm3(Predicted)
• LogP: 4.18190

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(1,1-Dimethylethyl) 5-Methyl (4S,5R)-2-(4-Methoxyphenyl)-4-phenyl-3,5-oxazolidinedicarboxylate is used in preparation of anti-tumor compound based on docetaxel side chain 2''-derivative.

Technology Process of (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate

There total 6 articles about (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate 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: 94.0%

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate (124605-42-1) + 4-methoxy-benzaldehyde (123-11-5) → (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate (670254-71-4,153652-75-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In toluene;

DOI:10.1002/jhet.5570420430

Reference yield:

(2R,3S)-3-phenylisoserine methyl ester (157240-36-3) → (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate (670254-71-4,153652-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / PPTS / toluene

With pyridinium p-toluenesulfonate; In toluene;

DOI:10.1002/jhet.5570420430

Reference yield:

(3R,4S)-3-hydroxy-4-(2',4'-dichlorophenyl)-2-(α-phenylethyl)azetidinone → (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate (670254-71-4,153652-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCl / methanol

1.2: H₂ / Pd/C

2.1: 94 percent / PPTS / toluene

With hydrogenchloride; pyridinium p-toluenesulfonate; In methanol; toluene;

DOI:10.1002/jhet.5570420430

upstream raw materials:

methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate

4-methoxy-benzaldehyde

di-tert-butyl dicarbonate

(2R,3S)-3-phenylisoserine methyl ester

Downstream raw materials:

acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique

Docetaxel

10-acetyldocetaxel

C₆₆H₇₃NO₁₆Si