(S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid

Base Information

• Chemical Name: (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid
• CAS No.: 182617-59-0
• Molecular Formula: C₃₈H₅₅N₅O₁₆
• Molecular Weight: 837.879
• Mol file: 182617-59-0.mol

Synonyms:(S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid

Chemical Property of (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid

There total 4 articles about (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic 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:

Pyruvic aldehyde dimethyl acetal (6342-56-9) → (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid (182617-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / NaH / dioxane / 8 h / 90 °C

2: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, room temperature, overnight

3: H₂ / Pd(OH)2/C / ethyl acetate / 760 Torr

4: 60 °C

5: 1) BOP, DIPEA, 2) TFA

With hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In 1,4-dioxane; ethyl acetate;

DOI:10.1016/0960-894X(96)00349-6

Reference yield:

benzyl 4,4-dimethoxy-3-oxobutyrate (182617-55-6) → (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid (182617-59-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaH / 1) DMF, 0 deg C, 1 h, 2) DMF, room temperature, overnight

2: H₂ / Pd(OH)2/C / ethyl acetate / 760 Torr

3: 60 °C

4: 1) BOP, DIPEA, 2) TFA

With hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In ethyl acetate;

DOI:10.1016/0960-894X(96)00349-6

Reference yield:

2-[4-((S)-2-Acetylamino-2-benzyloxycarbonyl-ethyl)-benzyl]-4,4-dimethoxy-3-oxo-butyric acid benzyl ester → (S)-2-{(2S,3S)-2-[(S)-2-((S)-2-{(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionylamino}-4-carboxy-butyrylamino)-4-carboxy-butyrylamino]-3-methyl-pentanoylamino}-pentanedioic acid (182617-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd(OH)2/C / ethyl acetate / 760 Torr

2: 60 °C

3: 1) BOP, DIPEA, 2) TFA

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium dihydroxide; In ethyl acetate;

DOI:10.1016/0960-894X(96)00349-6

upstream raw materials:

(S)-2-Acetylamino-3-[4-(4,4-dimethoxy-3-oxo-butyl)-phenyl]-propionic acid

Pyruvic aldehyde dimethyl acetal

benzyl 4,4-dimethoxy-3-oxobutyrate