([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester
• CAS No.: 214596-90-4
• Molecular Formula: C₃₈H₅₇N₃O₉
• Molecular Weight: 699.885

Synonyms:([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester

Chemical Property of ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester

There total 14 articles about ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl 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: 81.0%

Z-Leu-OH (2018-66-8) + {[1R,2S]-2-[4-(2-amino-1-hydroxyethyl)-phenoxy]-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl}carbamic acid tert-butyl ester (214596-93-7) → ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester (214596-90-4)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; 0 deg C to RT;

DOI:10.1016/S0040-4039(98)01589-5

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester (214596-90-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 73 percent / PPTS / CH₂Cl₂

2: 100 percent / KOH / methanol; H₂O / Heating

3: 85 percent / NaH / dimethylsulfoxide

4: 92 percent / Et₃N / CH₂Cl₂ / 0 deg C to RT

5: 93 percent / NaH₂PO₂*H₂O, pyridine / Raney Ni / acetic acid; H₂O

6: 96 percent / NaOMe / 0 °C

7: 94 percent / NH₄COOH / 10percent Pd/C / methanol

8: 81 percent / BOP, DIPEA / CH₂Cl₂ / 0 deg C to RT

With pyridine; potassium hydroxide; sodium hypophosphite; ammonium formate; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyric Acid; palladium on activated charcoal; nickel; In methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)01589-5

Reference yield:

4-(4S)-hydroxymethyl-5-(5R)-isopropyloxazolidin-2-one (125414-63-3,127870-57-9) → ([1R,2S]-2-{4-[2-(2S-benzyloxycarbonylamino-4-methylpentanoylamino)-1-hydroxyethyl]-phenoxy}-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl)carbamic acid tert-butyl ester (214596-90-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 73 percent / PPTS / CH₂Cl₂

2: 100 percent / KOH / methanol; H₂O / Heating

3: 85 percent / NaH / dimethylsulfoxide

4: 92 percent / Et₃N / CH₂Cl₂ / 0 deg C to RT

5: 93 percent / NaH₂PO₂*H₂O, pyridine / Raney Ni / acetic acid; H₂O

6: 96 percent / NaOMe / 0 °C

7: 94 percent / NH₄COOH / 10percent Pd/C / methanol

8: 81 percent / BOP, DIPEA / CH₂Cl₂ / 0 deg C to RT

With pyridine; potassium hydroxide; sodium hypophosphite; ammonium formate; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyric Acid; palladium on activated charcoal; nickel; In methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(98)01589-5

upstream raw materials:

Z-Leu-OH

{[1R,2S]-2-[4-(2-amino-1-hydroxyethyl)-phenoxy]-3-methyl-1-(tetrahydropyran-2-yloxymethyl)butyl}carbamic acid tert-butyl ester

3,4-dihydro-2H-pyran

4-fluorobenzonitrile

Downstream raw materials:

(2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-acetyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid

(2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid

(2S,3S)-3-{4-[2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-ethyl]-phenoxy}-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid pentafluorophenyl ester

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