5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

Base Information

• Chemical Name: 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid
• CAS No.: 162580-00-9
• Molecular Formula: C₂₅H₃₃NO₆
• Molecular Weight: 443.54

Synonyms:5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

Chemical Property of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

Chemical Property:

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Technology Process of 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

There total 3 articles about 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid 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: 96.0%

5(S)-[1(S)-(Boc-amino)-2-phenyl-ethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one (160431-24-3) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid (162580-00-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 10 ℃; for 0.666667h;

DOI:10.1002/ardp.19963290602

Reference yield:

4-methoxybenzyl iodide (70887-29-5) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid (162580-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 1 M (Me₃Si)2NLi / tetrahydrofuran / 1 h / -68 °C

2: 96 percent / 2 M aq. NaOH / ethanol / 0.67 h / 10 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;

DOI:10.1002/ardp.19963290602

Reference yield:

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate (133333-27-4) → 5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid (162580-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 1 M (Me₃Si)2NLi / tetrahydrofuran / 1 h / -68 °C

2: 96 percent / 2 M aq. NaOH / ethanol / 0.67 h / 10 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol;

DOI:10.1002/ardp.19963290602

upstream raw materials:

5(S)-[1(S)-(Boc-amino)-2-phenyl-ethyl]-3(R)-(p-methoxy-phenylmethyl)-dihydrofuran-2-(3H)-one

4-methoxybenzyl iodide

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

Downstream raw materials:

5(S)-(Boc-amino)-4(S)-(tert-butyldimethylsilyloxy)-6-phenyl-2(R)-(p-methoxyphenylmethyl)-hexanoic acid

[(1S,2S,4R)-1-Benzyl-4-[(S)-1-((S)-1-benzyl-2-morpholin-4-yl-2-oxo-ethylcarbamoyl)-2-methyl-propylcarbamoyl]-2-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenyl)-pentyl]-carbamic acid tert-butyl ester

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