Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester
CAS No.:160974-73-2
Molecular Formula:C₂₈H₃₁NO₁₂
Molecular Weight:573.554
Hs Code.:

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-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: 75.4%

: 622-33-3
N-benzyloxyamine

: 76306-75-7
2,3,4,6-O-tetraacetyl-4-β-D-glucopyranosyloxybenzoic acid

: 160974-73-2
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1248/bpb.18.208

Reference yield:

: 94-18-8
Benzyl 4-hydroxybenzoate

: 160974-73-2
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 65 percent / Ag₂O / quinoline

2: 1.45 g / H₂ / 10 percent Pd-C / tetrahydrofuran / 24 h / 20 °C

3: 75.4 percent / dicyclohexylcarbodiimide; 1-hydroxybenzotriazol; triethylamine / CH₂Cl₂; dimethylformamide / 0 °C

With hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; palladium on activated charcoal; In tetrahydrofuran; quinoline; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Hydrogenolysis / 3: Acylation;
DOI:10.1248/bpb.18.208

Reference yield:

: 160974-72-1
4-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-benzoic acid benzyl ester

: 160974-73-2
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-benzyloxycarbamoyl-phenoxy)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.45 g / H₂ / 10 percent Pd-C / tetrahydrofuran / 24 h / 20 °C

2: 75.4 percent / dicyclohexylcarbodiimide; 1-hydroxybenzotriazol; triethylamine / CH₂Cl₂; dimethylformamide / 0 °C

With hydrogen; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation;
DOI:10.1248/bpb.18.208