ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside
• CAS No.: 144220-49-5
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 144220-49-5.mol

Synonyms:ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside

Chemical Property of ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside

There total 1 articles about ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside 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: 63.0%

4-methoxy-benzoyl chloride (100-07-2) + ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (23339-15-3) → ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside (144220-49-5)

Guidance literature:

With pyridine; In benzene; at 0 ℃; for 2h;

DOI:10.1002/ardp.19923250808

Reference yield:

ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside (144220-49-5) → 4-Methoxy-benzoic acid (2S,4R)-4-(4-isobutyrylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydro-2H-pyran-2-ylmethyl ester (144220-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) imidazole, NaH / 1.) THF, 0 deg C, 60 min, 2.) r.t., 60 min

2: 36 percent / tri-n-butyltin hydride, α,α'-azoisobutyronitrile / toluene / 5 h / Heating

3: 1.) hexamethyldisilazane, NH₄SO₄ / 2.) trimethylsilyl trifluoromethanesulfonate / 1.) reflux, 4 - 6 h, 2.) acetonitrile, 0 deg C, 2 h

With 1H-imidazole; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; trimethylsilyl trifluoromethanesulfonate; In toluene;

DOI:10.1002/ardp.19923250808

Reference yield:

ethyl 2,3-dideoxy-6-O-(4-methoxybenzoyl)-α-D-erythro-hex-2-enopyranoside (144220-49-5) → 4-Methoxy-benzoic acid (2S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydro-2H-pyran-2-ylmethyl ester (144220-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) imidazole, NaH / 1.) THF, 0 deg C, 60 min, 2.) r.t., 60 min

2: 36 percent / tri-n-butyltin hydride, α,α'-azoisobutyronitrile / toluene / 5 h / Heating

3: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0.25 h / 0 °C

With 1H-imidazole; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium hydride; trimethylsilyl trifluoromethanesulfonate; In toluene; acetonitrile;

DOI:10.1002/ardp.19923250808

upstream raw materials:

4-methoxy-benzoyl chloride

ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Downstream raw materials:

1-(2,3,4-trideoxy-β-D-glycero-hex-3-enopyranosyl)thymine

ethyl 6-O-(4-methoxybenzoyl)-2,3,4-trideoxy-α-D-glycero-hex-2-enopyranoside

ethyl 6-O-(4-methoxybenzoyl)-2,3,4-trideoxy-α-D-glycero-hex-3-enopyranoside

4-Methoxy-benzoic acid (2S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydro-2H-pyran-2-ylmethyl ester