(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester

Base Information

• Chemical Name: (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester
• CAS No.: 871483-69-1
• Molecular Formula: C₄₀H₄₉N₃O₉
• Molecular Weight: 715.844
• Mol file: 871483-69-1.mol

Synonyms:

Chemical Property of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester

There total 8 articles about (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl 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:

isobutyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (137100-81-3) → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester (871483-69-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / Pd(PPh₃)4 / tetrahydrofuran / Heating

2: 98 percent / K₂CO₃; MeOH

3: 96 percent / imidazole

4: 85 percent / ClCO₂ClCHCH₃

5: HF*Py

With 1H-imidazole; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbonochloridic acid 1-chloro-ethyl ester; potassium carbonate; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

D-glucal triacetate (2873-29-2) → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester (871483-69-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / BiCl₃ / acetonitrile

2: 80 percent / Pd(PPh₃)4 / tetrahydrofuran / Heating

3: 98 percent / K₂CO₃; MeOH

4: 96 percent / imidazole

5: 85 percent / ClCO₂ClCHCH₃

6: HF*Py

With 1H-imidazole; methanol; bismuth(III) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbonochloridic acid 1-chloro-ethyl ester; potassium carbonate; pyridine hydrogenfluoride; In tetrahydrofuran; acetonitrile; 1: Ferrier glycosidation;

DOI:10.1016/j.bmcl.2005.08.062

Reference yield:

N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(2-{[2-(tert-butyl-dimethyl-silanyloxymethyl)-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl]-methyl-amino}-acetylamino)-succinamic acid benzyl ester → (S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-{2-[((2S,3S,6S)-2-hydroxymethyl-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl)-methyl-amino]-acetylamino}-succinamic acid benzyl ester (871483-69-1)

Guidance literature:

With pyridine hydrogenfluoride;

DOI:10.1016/j.bmcl.2005.08.062

upstream raw materials:

[(2S,3S,6S)-3-(Benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-yl]-methanol

[2-(tert-butyl-dimethyl-silanyloxymethyl)-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl]-methyl-amine

Acetic acid (2S,3S,6S)-3-(benzyl-methyl-amino)-6-isobutoxy-3,6-dihydro-2H-pyran-2-ylmethyl ester

benzyl-[2-(tert-butyl-dimethyl-silanyloxymethyl)-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl]-methyl-amine

Downstream raw materials:

N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(2-{[2-(3-9H-fluoren-9-yl-propionyloxymethyl)-6-isobutoxy-3,6-dihydro-2H-pyran-3-yl]-methyl-amino}-acetylamino)-succinamic acid benzyl ester

(S)-N-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-3-(2-{[(2S,3S,6S)-6-isobutoxy-2-(3-phenyl-propionyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-methyl-amino}-acetylamino)-succinamic acid benzyl ester