4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester

Base Information

• Chemical Name: 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester
• CAS No.: 173918-50-8
• Molecular Formula: C₂₈H₂₈F₂N₂O₈
• Molecular Weight: 558.536

Synonyms:4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester

Chemical Property of 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester

Chemical Property:

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Technology Process of 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester

There total 2 articles about 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) 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: 46.0%

Ethyl bromodifluoroacetate (667-27-6) + (R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosinal (173918-49-5) → 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester (173918-50-8)

Guidance literature:

With zinc; In tetrahydrofuran; reflux; rt, 15 h;

DOI:10.1016/0040-4020(95)00896-G

Reference yield:

(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosine methyl ester → 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester (173918-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / ddisobutylaluminium hydride / diethyl ether; toluene; hexane / 0.17 h / -78 °C

2: 46 percent / zinc / tetrahydrofuran / reflux; rt, 15 h

With diisobutylaluminium hydride; zinc; In tetrahydrofuran; diethyl ether; hexane; toluene;

DOI:10.1016/0040-4020(95)00896-G

Reference yield: 57.0%

4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl) pentanoic acid ethyl ester (173918-50-8) → 4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)pentanamide (173918-51-9)

Guidance literature:

With ammonia; In diethyl ether; at -78 ℃;

DOI:10.1016/0040-4020(95)00896-G

upstream raw materials:

Ethyl bromodifluoroacetate

(R,S)-N-(4-nitrobenzyloxycarbonyl)-O-benzyl-tyrosinal

Downstream raw materials:

4-(4-nitrobenzyloxycarbonylamino)-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)pentanamide

[4-Amino-5-(4-benzyloxy-phenyl)-2,2-difluoro-3-hydroxy-pentyl]-carbamic acid tert-butyl ester

N⁴-(4-nitrobenzyloxycarbonyl)-N¹-tert-butoxycarbonyl-2,2-difluoro-3-hydroxy-5-(4-benzyloxyphenyl)-1,4-pentanediamine

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