Butanamide, N-[(1R,2R)-2-(acetyloxy)-3-oxo-1-phenylpropyl]-2-azido-4-(benzoyloxy)- 3-(methoxymethoxy)-N-methyl-, (2S,3S)-

Base Information

• Chemical Name: Butanamide, N-[(1R,2R)-2-(acetyloxy)-3-oxo-1-phenylpropyl]-2-azido-4-(benzoyloxy)- 3-(methoxymethoxy)-N-methyl-, (2S,3S)-
• CAS No.: 501954-78-5
• Molecular Formula: C25H28N4O8
• Molecular Weight: 512.519
• Mol file: 501954-78-5.mol

Synonyms:

Chemical Property of Butanamide, N-[(1R,2R)-2-(acetyloxy)-3-oxo-1-phenylpropyl]-2-azido-4-(benzoyloxy)- 3-(methoxymethoxy)-N-methyl-, (2S,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Butanamide, N-[(1R,2R)-2-(acetyloxy)-3-oxo-1-phenylpropyl]-2-azido-4-(benzoyloxy)- 3-(methoxymethoxy)-N-methyl-, (2S,3S)-

There total 17 articles about Butanamide, N-[(1R,2R)-2-(acetyloxy)-3-oxo-1-phenylpropyl]-2-azido-4-(benzoyloxy)- 3-(methoxymethoxy)-N-methyl-, (2S,3S)- 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: 99.0%

Benzoic acid (2S,3S)-3-[((1R,2R)-2-acetoxy-3-hydroxy-1-phenyl-propyl)-methyl-carbamoyl]-3-azido-2-methoxymethoxy-propyl ester (501954-95-6) → Benzoic acid (2S,3S)-3-[((1R,2R)-2-acetoxy-3-oxo-1-phenyl-propyl)-methyl-carbamoyl]-3-azido-2-methoxymethoxy-propyl ester (501954-78-5)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.3987/COM-02-S42

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (2S,3S)-3-[((1R,2R)-2-acetoxy-3-oxo-1-phenyl-propyl)-methyl-carbamoyl]-3-azido-2-methoxymethoxy-propyl ester (501954-78-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 76 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

2: 88 percent / (i-Pr)2NEt / CH₂Cl₂ / 40 °C

3: 100 percent / DDQ / CH₂Cl₂; H₂O / 20 °C

4: PDC / dimethylformamide / 20 °C

5: (COCl)2

6: (Me₂CH)2NEt / tetrahydrofuran / 20 °C

7: 82 percent / aq. HCl / tetrahydrofuran / 50 °C

8: 83 percent / imidazole / CH₂Cl₂

9: 99 percent / TEA; DMAP / CH₂Cl₂

10: 98 percent / aq. HCl / tetrahydrofuran / 50 °C

11: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂

With 1H-imidazole; hydrogenchloride; dmap; dipyridinium dichromate; oxalyl dichloride; TEA; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 11: Swern oxidation;

DOI:10.3987/COM-02-S42

Reference yield:

[(R)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-methyl-amine → Benzoic acid (2S,3S)-3-[((1R,2R)-2-acetoxy-3-oxo-1-phenyl-propyl)-methyl-carbamoyl]-3-azido-2-methoxymethoxy-propyl ester (501954-78-5)

Guidance literature:

Multi-step reaction with 6 steps

1: (Me₂CH)2NEt / tetrahydrofuran / 20 °C

2: 82 percent / aq. HCl / tetrahydrofuran / 50 °C

3: 83 percent / imidazole / CH₂Cl₂

4: 99 percent / TEA; DMAP / CH₂Cl₂

5: 98 percent / aq. HCl / tetrahydrofuran / 50 °C

6: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂

With 1H-imidazole; hydrogenchloride; dmap; oxalyl dichloride; TEA; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 6: Swern oxidation;

DOI:10.3987/COM-02-S42

upstream raw materials:

Benzoic acid (2S,3S)-3-[((1R,2R)-2-acetoxy-3-hydroxy-1-phenyl-propyl)-methyl-carbamoyl]-3-azido-2-methoxymethoxy-propyl ester

benzoyl chloride

2,2,2-Trifluoro-acetimidic acid (2S,3R)-3-phenyl-oxiranylmethyl ester

Benzoic acid (2S,3R)-3-azido-4-hydroxy-2-methoxymethoxy-butyl ester

Refernces