methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

Base Information

Chemical Name:methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate
CAS No.:391640-93-0
Molecular Formula:C₂₁H₂₅ClNO₅P
Molecular Weight:437.86
Hs Code.:

Synonyms:methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

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Chemical Property of methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

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Technology Process of methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

There total 6 articles about methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate 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: 29.0%

: 391642-54-9
N-(3-hydroxypropyl)-D-valine methyl ester

: 391642-63-0
4-(4-chlorophenoxy)phenylphosphonic dichloride

: 391640-93-0
methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.bmc.2003.09.015

Reference yield:

D-Valine methyl ester hydrochloride: 7146-15-8
D-Valine methyl ester hydrochloride

: 391640-93-0
methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 61 percent / NaBH₃CN / methanol / 20 °C

2.1: 69 percent / N,N-diisopropylethylamine / dimethylsulfoxide / 40 °C

3.1: 9-BBN / tetrahydrofuran / 4.5 h / 20 °C

3.2: 17.1 g / NaOH; H₂O₂ / H₂O / 1.5 h / 0 °C

4.1: 68 percent / H₂ / Pd/C / ethanol / 2.5 h

5.1: 29 percent / NMM / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2003.09.015

Reference yield:

: 210917-86-5
N-benzyl-D-valine methyl ester

: 391640-93-0
methyl (2R,αR)-2-[4-(4-chlorophenoxy)phenyl]-α-(1-methylethyl)-2-oxo-1,3,2-oxazaphosphorinane-3-acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 69 percent / N,N-diisopropylethylamine / dimethylsulfoxide / 40 °C

2.1: 9-BBN / tetrahydrofuran / 4.5 h / 20 °C

2.2: 17.1 g / NaOH; H₂O₂ / H₂O / 1.5 h / 0 °C

3.1: 68 percent / H₂ / Pd/C / ethanol / 2.5 h

4.1: 29 percent / NMM / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.bmc.2003.09.015