Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester
• CAS No.: 849063-78-1
• Molecular Formula: C₄₉H₆₂N₅O₂₀P
• Molecular Weight: 1072.03
• Mol file: 849063-78-1.mol

Synonyms:Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl 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: 65.0%

AcNHSer(OBn)Ser(OBn)SerAlaCONH2 (849063-77-0) + (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite (637004-85-4) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester (849063-78-1)

Guidance literature:

AcNHSer(OBn)Ser(OBn)SerAlaCONH₂; (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite; With 1H-tetrazole; In N,N-dimethyl-formamide; acetonitrile; at 65 ℃; for 3.5h;

With tert.-butylhydroperoxide; In decane; N,N-dimethyl-formamide; acetonitrile; at -40 ℃; for 1.5h;

DOI:10.1021/jo048443z

Reference yield:

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite (849063-81-6) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester (849063-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

2.1: 1H-tetrazole / dimethylformamide; acetonitrile / 3.5 h / 65 °C

2.2: 65 percent / tBuOOH / decane; acetonitrile; dimethylformamide / 1.5 h / -40 °C

With 1H-tetrazole; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo048443z

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester (849063-78-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / diisopropyl(ethyl)amine / CH₂Cl₂ / 6 h / 20 °C

2.1: 79 percent / 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

3.1: 1H-tetrazole / dimethylformamide; acetonitrile / 3.5 h / 65 °C

3.2: 65 percent / tBuOOH / decane; acetonitrile; dimethylformamide / 1.5 h / -40 °C

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo048443z

upstream raw materials:

AcNHSer(OBn)Ser(OBn)SerAlaCONH₂

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-hydroxy-phosphoryloxy}-tetrahydro-pyran-4-yl ester