(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester

Base Information

• Chemical Name: (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester
• CAS No.: 762267-60-7
• Molecular Formula: C₂₆H₃₅N₅O₆S
• Molecular Weight: 545.66
• Mol file: 762267-60-7.mol

Synonyms:(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester

Chemical Property of (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester

There total 12 articles about (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl 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: 75.0%

2-[(2S,3S,6S)-2-allyloxy-6-(azidomethyl)-3,6-dihydro-2H-pyran-3-yl]acetic acid (762267-59-4) + Phe-Cys-OMe trifluoroacetate → (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester (762267-60-7)

Guidance literature:

With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/ejoc.200400166

Reference yield:

allyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside (121703-30-8) → (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester (762267-60-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 99 percent / KOH / methanol / 2 h / 20 °C

2: 95 percent / DIAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

3: 99 percent / sodium methoxide / methanol / 2 h

4: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 85 percent / hydroquinone; propionic acid / 20 h / 140 °C

6: 95 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

7: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

8: 76 percent / NaN₃ / dimethylformamide / 60 °C

9: 72 percent / methanol / 3 h / 20 °C

10: 93 percent / LiOH / tetrahydrofuran; H₂O / 3.5 h / 20 °C

11: 75 percent / HOBt; EDC; DMAP / Et₃N / dimethylformamide / 20 °C

With dmap; potassium hydroxide; lithium hydroxide; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; benzotriazol-1-ol; propionic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydroquinone; triphenylphosphine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200400166

Reference yield:

D-glucal triacetate (2873-29-2) → (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methylsulfanyl-butyric acid methyl ester (762267-60-7)

Guidance literature:

Multi-step reaction with 12 steps

1: 91 percent / FeCl₃ / acetonitrile / 0.5 h

2: 99 percent / KOH / methanol / 2 h / 20 °C

3: 95 percent / DIAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

4: 99 percent / sodium methoxide / methanol / 2 h

5: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 85 percent / hydroquinone; propionic acid / 20 h / 140 °C

7: 95 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

8: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

9: 76 percent / NaN₃ / dimethylformamide / 60 °C

10: 72 percent / methanol / 3 h / 20 °C

11: 93 percent / LiOH / tetrahydrofuran; H₂O / 3.5 h / 20 °C

12: 75 percent / HOBt; EDC; DMAP / Et₃N / dimethylformamide / 20 °C

With dmap; potassium hydroxide; lithium hydroxide; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; iron(III) chloride; benzotriazol-1-ol; propionic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydroquinone; triphenylphosphine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/ejoc.200400166

upstream raw materials:

2-[(2S,3S,6S)-2-allyloxy-6-(azidomethyl)-3,6-dihydro-2H-pyran-3-yl]acetic acid

allyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

D-glucal triacetate

ethyl 2-[(2S,3S,6S)-2-allyloxy-6-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-yl]acetate