methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside
• CAS No.: 149057-38-5
• Molecular Formula: C₁₄H₁₇FO₅
• Molecular Weight: 284.284
• Mol file: 149057-38-5.mol

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside

There total 1 articles about methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside 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: 42.0%

methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α,β-D-ribo-hexopyranosid-3-ulose → methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-glucopyranoside (115216-41-6) + methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside (149057-38-5) + (4aR,6R,7R,8R,8aS)-7-Fluoro-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:

With sodium tetrahydroborate; In ethanol; at -20 - 20 ℃;

DOI:10.1016/S0008-6215(98)00325-5

Reference yield: 91.0%

acetic anhydride (108-24-7) + methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside (149057-38-5) → methyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1016/S0008-6215(98)00325-5

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-fluoro-α-D-allopyranoside (149057-38-5) → methyl 3-O-acetyl-4-O-benzoyl-2,6-dideoxy-2-fluoro-β-L-talopyranoside (228850-12-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine; 4-dimethylaminopyridine / 20 °C

2: 87 percent / NBS; BaCO₃ / CCl₄ / 0.33 h / 75 - 80 °C

3: 93 percent / DBU / benzene / 2 h / Heating

4: 89 percent / hydrogen / Pd; BaSO₄ / ethyl acetate / 0.5 h

With pyridine; dmap; N-Bromosuccinimide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; barium carbonate; barium sulfate; palladium; In tetrachloromethane; ethyl acetate; benzene; 1: Acetylation / 2: Ring cleavage / 3: Elimination / 4: Hydrogenation;

DOI:10.1016/S0008-6215(98)00325-5

Downstream raw materials:

methyl 3-O-acetyl-4-O-benzoyl-2,6-dideoxy-2-fluoro-β-L-talopyranoside

methyl 3-O-acetyl-4-O-benzoyl-2,6-dideoxy-2-fluoro-α-D-ribo-hex-5-enopyranoside

methyl 3-O-acetyl-4-O-benzoyl-6-bromo-2,6-dideoxy-2-fluoro-α-D-allopyranoside