(4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid

Base Information

• Chemical Name: (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid
• CAS No.: 191407-88-2
• Molecular Formula: C₃₀H₄₇N₃O₈
• Molecular Weight: 577.718

Synonyms:(4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid

Chemical Property of (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid

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Technology Process of (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid

There total 8 articles about (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic 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: 60.0%

tert-butyl (2S,3R)-3-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-2-(3-hydroxypropyl)-5-methylhexanoate (191407-87-1) → (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid (191407-88-2)

Guidance literature:

With ruthenium trichloride; periodic acid; In tetrachloromethane; acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1021/jm010127e

Reference yield:

4-benzyl 1-tert-butyl (2S,3R)-2-(3-hydroxypropyl)-3-isobutylbutanedioate (191406-75-4) → (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid (191407-88-2)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 3 h

2: 77 percent / BOP; DIEA / dimethylformamide

3: 60 percent / RuCl₃; aq. H₅IO₆ / CCl₄; acetonitrile / 1.5 h / 20 °C

With ruthenium trichloride; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm010127e

Reference yield:

(2R,3S)-3-(tert-butoxycarbonyl)-2-isobutylhex-5-enoic acid benzyl ester (191406-74-3) → (4S,5R)-5-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-4-(tert-butoxycarbonyl)-7-methyloctanoic acid (191407-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

1.2: 64 percent / aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

2.1: H₂ / Pd/C / methanol / 3 h

3.1: 77 percent / BOP; DIEA / dimethylformamide

4.1: 60 percent / RuCl₃; aq. H₅IO₆ / CCl₄; acetonitrile / 1.5 h / 20 °C

With ruthenium trichloride; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; periodic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm010127e

upstream raw materials:

tert-butyl (2S,3R)-3-[({(1S)-5-{[(benzyloxy)carbonyl]amino}-1-[(methylamino)carbonyl]pentyl}amino)carbonyl]-2-(3-hydroxypropyl)-5-methylhexanoate

Boc-Lys(Z)-OH

N^ε-[(benzyloxy)carbonyl]-L-lysine N-methylamide

4-benzyl 1-tert-butyl (2S,3R)-2-(3-hydroxypropyl)-3-isobutylbutanedioate

Downstream raw materials:

(2S,11S,12R)-N¹¹-(benzyloxy)-12-isobutyl-N²-methyl-8,13-dioxo-1,7-diazacyclotridecane-2,11-dicarboxamide

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