(3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester

Base Information

• Chemical Name: (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester
• CAS No.: 1008777-00-1
• Molecular Formula: C₂₅H₃₃NO₆
• Molecular Weight: 443.54
• Mol file: 1008777-00-1.mol

Synonyms:(3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester

Chemical Property of (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester

There total 2 articles about (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic 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: 39.0%

O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal (82689-15-4) + ethyl acetate (141-78-6) → (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester (1008777-00-1) + (3S,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester (1008776-84-8)

Guidance literature:

ethyl acetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Further stages.;

DOI:10.1016/j.bmcl.2007.11.005

Reference yield:

3-(tert-butoxycarbonylamino)-2-oxo-4-(benzyloxy)benzenepentanoic acid ethyl ester (1108593-76-5) → (3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester (1008777-00-1) + (3S,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester (1008776-84-8)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.3987/COM-08-S(N)108

Reference yield: 96.0%

(3R,4S)-5-[4-(benzyloxy)phenyl]-4-(tert-butoxycarbonylamino)-3-hydroxypentanoic acid ethyl ester (1008777-00-1) + allyl ethyl carbonate (1469-70-1) → (3R,4S)-ethyl 3-(allyloxy)-5-(4-(benzyloxy)phenyl)-4-(tert-butoxycarbonylamino)pentanoate (1259939-03-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; at 65 ℃; for 4h; Inert atmosphere;

DOI:10.1039/c0ob00352b

upstream raw materials:

O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal

ethyl acetate

3-(tert-butoxycarbonylamino)-2-oxo-4-(benzyloxy)benzenepentanoic acid ethyl ester

Downstream raw materials:

(3R,4S)-ethyl 3-(allyloxy)-5-(4-(benzyloxy)phenyl)-4-(tert-butoxycarbonylamino)pentanoate