methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate)

Base Information

• Chemical Name: methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate)
• CAS No.: 1320281-75-1
• Molecular Formula: C₂₂H₂₃FO₆S
• Molecular Weight: 434.485
• Mol file: 1320281-75-1.mol

Synonyms:

Chemical Property of methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate)

There total 9 articles about methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate) 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:

C19H19FO4S (1320281-52-4) → methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate) (1320281-75-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

2: toluene-4-sulfonic acid / methanol

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 5 h / 0 - 20 °C

4: potassium carbonate / N,N-dimethyl-formamide / 20 °C

5: pyridine / 20 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol2016862

Reference yield:

C19H21FO4S (1320281-55-7) → methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate) (1320281-75-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 5 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3: pyridine / 20 °C

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium carbonate; In water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol2016862

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranoside uronate (1320281-48-8) → methyl (phenyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranosyluronate) (1320281-75-1)

Guidance literature:

Multi-step reaction with 7 steps

1: methanol; sodium methylate / 20 °C

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

4: toluene-4-sulfonic acid / methanol

5: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 5 h / 0 - 20 °C

6: potassium carbonate / N,N-dimethyl-formamide / 20 °C

7: pyridine / 20 °C

With pyridine; methanol; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium methylate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol2016862

upstream raw materials:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-1-thio-α-D-mannopyranoside uronate

C₁₂H₁₅FO₄S

C₁₉H₁₉FO₄S

C₂₆H₂₅FO₄S

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-(methyl 4-O-acetyl-3-O-benzyl-2-deoxy-2-fluoro-β-D-mannopyranosyl uronate)-α-D-glucopyranoside