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

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxy-propoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 160956-46-7
• Molecular Formula: C₂₄H₃₂O₁₁
• Molecular Weight: 496.511
• Mol file: 160956-46-7.mol

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

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

There total 1 articles about Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxy-propoxy)-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: 90.0%

3-benzyloxypropan-1-ol (4799-68-2) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxy-propoxy)-tetrahydro-pyran-4-yl ester (160956-46-7)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In acetonitrile; benzene; for 12h; Ambient temperature;

DOI:10.1016/0008-6215(94)80046-4

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxy-propoxy)-tetrahydro-pyran-4-yl ester (160956-46-7) → N6-benzoyl-9-(2,3-di-O-benzoyl-β-D-arabinofuranosyl)adenine 5'-<(prop-3-yl tetra-O-acetyl-β-D-galactopyranoside)-1-yl> 2-cyanoethylphosphate

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / 10percent Pd/C / ethanol / 5 h / 2280 Torr

2: diisopropylethylamine / CH₂Cl₂ / 0.25 h

3: tetrazole / CH₂Cl₂; acetonitrile / 15 h / Ambient temperature

4: I₂ / CH₂Cl₂; acetonitrile

With 1H-tetrazole; hydrogen; iodine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(94)80046-4

Reference yield:

Acetic acid (2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(3-benzyloxy-propoxy)-tetrahydro-pyran-4-yl ester (160956-46-7) → N6-benzoyl-9-(2,3-di-O-benzoyl-β-D-galactopyranosyl)adenine 5'-<(prop-3-yl tetra-O-acetyl-β-D-galactopyranoside)-1-yl> 2-cyanoethylthio-phosphate

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / H₂ / 10percent Pd/C / ethanol / 5 h / 2280 Torr

2: diisopropylethylamine / CH₂Cl₂ / 0.25 h

3: tetrazole / CH₂Cl₂; acetonitrile / 15 h / Ambient temperature

4: S / CH₂Cl₂; acetonitrile; toluene

With 1H-tetrazole; hydrogen; sulfur; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; dichloromethane; toluene; acetonitrile;

DOI:10.1016/0008-6215(94)80046-4

upstream raw materials:

3-benzyloxypropan-1-ol

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside