(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester

Base Information

• Chemical Name: (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester
• CAS No.: 134081-17-7
• Molecular Formula: C₁₈H₂₇NO₆
• Molecular Weight: 353.415

Synonyms:(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester

Chemical Property of (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester

Chemical Property:

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Technology Process of (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester

There total 1 articles about (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester 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:

N-(tert-butyloxycarbonyl)-L-tyrosinal (134081-15-5) + ethyl acetate (141-78-6) → (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester (134081-17-7) + (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester (134081-16-6)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h;

DOI:10.1021/jm00111a054

Reference yield: 48.0%

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester (134081-17-7) → (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid (1008776-95-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2007.11.005

Reference yield:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid ethyl ester (134081-17-7) → (3R,4S)-tert-butoxycarbonylamino-3-[(1R)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]-5-(p-[(1R)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]phenyl)-pentanoic acid ethyl ester (1008776-97-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1016/j.bmcl.2007.11.005

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-tyrosinal

ethyl acetate

Downstream raw materials:

(3R,4S)-tert-butoxycarbonylamino-3-[(1R)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]-5-(p-[(1R)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]phenyl)-pentanoic acid ethyl ester

(3R,4S)-tert-butoxycarbonylamino-3-[(1S)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]-5-(p-[(1S)-1-methoxy-1-(trifluoromethyl)phenylacetoxy]phenyl)-pentanoic acid ethyl ester

(3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-(p-hydroxyphenyl)-pentanoic acid

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