methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate

Base Information

• Chemical Name: methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate
• CAS No.: 1214912-86-3
• Molecular Formula: C₂₂H₂₈FNO₁₀S
• Molecular Weight: 517.529
• Mol file: 1214912-86-3.mol

Synonyms:methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate

Chemical Property of methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate

There total 4 articles about methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate 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: 76.0%

methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-D-erythro-α-L-manno-non-2-ulopyranosonate (1214912-85-2) + phenylcarbonochloridothioate (1005-56-7) → methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate (1214912-86-3)

Guidance literature:

With pyridine; In dichloromethane; at -40 - 20 ℃;

Reference yield:

N-acetyl-D-mannosamine (14131-64-7) → methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate (1214912-86-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-acetylneuraminic aldolase / water / 120 h / 20 °C / Enzymatic reaction

1.2: dowex 1x2 200 ion exchange resin

2.1: trifluoroacetic acid / 16 h / 20 °C

3.1: triethylamine; toluene-4-sulfonic acid / acetone / 4 h / 20 °C

4.1: pyridine / dichloromethane / 4 h / -40 - 20 °C

With pyridine; N-acetylneuraminic aldolase; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In dichloromethane; water; acetone; 4.1: |Barton-McCombie Deoxygenation;

DOI:10.1016/j.carres.2013.03.026

Reference yield:

3-fluoro-N-acetylneuraminic acid → methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-4-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate (1214912-86-3)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid / 16 h / 20 °C

2: triethylamine; toluene-4-sulfonic acid / acetone / 4 h / 20 °C

3: pyridine / dichloromethane / 4 h / -40 - 20 °C

With pyridine; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In dichloromethane; acetone; 3: |Barton-McCombie Deoxygenation;

DOI:10.1016/j.carres.2013.03.026

upstream raw materials:

methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-D-erythro-α-L-manno-non-2-ulopyranosonate

phenylcarbonochloridothioate

N-acetyl-D-mannosamine