(R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid

Base Information

• Chemical Name: (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid
• CAS No.: 332113-64-1
• Molecular Formula: C₂₀H₂₂NO₆P
• Molecular Weight: 403.372

Synonyms:(R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid

Chemical Property of (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid

Chemical Property:

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Technology Process of (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid

There total 4 articles about (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic 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: 100.0%

(R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid tert-butyl ester (332113-62-9) → (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid (332113-64-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jm0308491

Reference yield:

(R)-<1-<(Benzyloxycarbonyl)amino>-2-phenylethyl>phosphonous acid → (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid (332113-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / HMDS / 3 h / 110 °C

2: 100 percent / TFA / CH₂Cl₂ / 1 h / 20 °C

With 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; In dichloromethane; 1: Michael addition;

DOI:10.1021/jm0308491

Reference yield:

((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid (118636-74-1) → (R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid (332113-64-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

2: CH₂Cl₂ / 24 h / 20 °C

3: TFA / CH₂Cl₂ / 1 h / 20 °C

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ol0069103

upstream raw materials:

(R)-2-[(1-benzyloxycarbonylamino-2-phenylethyl)hydroxyphosphinoylmethyl]acrylic acid tert-butyl ester

((R)-1-(((benzyloxy)carbonyl)amino)-2-phenylethyl)phosphinic acid

Downstream raw materials:

[(R),(S)]-(1-benzyloxycarbonylamino-2-phenylethyl){2-[1-carbamoyl-2-(1H-indol-3-yl)ethylcarbamoyl]allyl}phosphinic acid

[(R),(R,S),(S)]-(1-benzyloxycarbonylamino-2-phenylethyl)-{3-(4-bromo-2-trifluoromethoxyphenylsulfanyl)-2-[1-carbamoyl-2-(1H-indol-3-yl)ethylcarbamoyl]propyl}phosphinic acid

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