methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

Base Information

Chemical Name:methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate
CAS No.:52816-32-7
Molecular Formula:C₃₄H₄₈N₄O₉
Molecular Weight:656.777
Hs Code.:

Synonyms:methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

There total 21 articles about methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate 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: 95.0%

: 52816-29-2
N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

: (S)-5-(Acetyl-benzyloxy-amino)-2-amino-pentanoic acid methyl ester; hydrochloride

: 52816-32-7
methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;
DOI:10.3987/COM-14-S(K)67

Reference yield: 67.0%

: 90195-04-3
(S)-5-(Acetyl-benzyloxy-amino)-2-amino-pentanoic acid methyl ester

: 52816-29-2
N²-(tert-butoxycarbonyl)-N⁵-acetyl-N⁵-(benzyloxy)-L-ornithine

: 52816-32-7
methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

Guidance literature:: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In acetonitrile; for 16h; Ambient temperature;
DOI:10.1021/jo00187a023

Reference yield:

: 90194-99-3
tert-butyl (S)-2-<(tert-butyloxycarbonyl)amino>-5-hydroxypentanoate

: 52816-32-7
methyl(S)-5-[N-(benzyloxy)acetamido]-2-{(S)-5-[N-(benzyloxy)acetamido]-2-[(tert-butoxy-carbonyl)amino]pentanamide}pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 66 percent / PPh₃, DEAD / tetrahydrofuran / 5 h / Ambient temperature

2: 55 percent / H₂ / 5percent Pd/C / ethyl acetate / 760 Torr / 1.) 1.5 h, 0 deg C, 2.) 2.5 h, room temperature

3: 57 percent / CF₃COOH / 1 h / Ambient temperature

4: 85 percent / NEt₃ / tetrahydrofuran; H₂O / 16 h / Ambient temperature

5: 67 percent / 2-ethoxy-N-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) / acetonitrile / 16 h / Ambient temperature

With hydrogen; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; water; ethyl acetate; acetonitrile;
DOI:10.1021/jo00187a023