methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate

Base Information

• Chemical Name: methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate
• CAS No.: 931415-42-8
• Molecular Formula: C₂₇H₃₆N₂O₁₂
• Molecular Weight: 580.589
• Mol file: 931415-42-8.mol

Synonyms:methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate

Chemical Property of methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate

There total 5 articles about methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate 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%

O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate (869996-05-4) + vorinostat (149647-78-9) → methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate (931415-42-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 20 ℃;

DOI:10.1021/jo0701839

Reference yield: 73.0%

suberanilic acid (149648-52-2) + (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-aminooxy-tetrahydro-pyran-2-carboxylic acid methyl ester (319926-20-0) → methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate (931415-42-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmcl.2006.11.042

Reference yield:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) → methyl 2,3,4-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-glucopyranosyluronate (931415-42-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

2: 76 percent / TMSOTf / CH₂Cl₂ / -20 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In dichloromethane;

DOI:10.1021/jo0701839

upstream raw materials:

suberanilic acid

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-aminooxy-tetrahydro-pyran-2-carboxylic acid methyl ester

O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate

vorinostat

Downstream raw materials:

Vorinostat O-Glucuronide

3,4,5-trihydroxy-6-(7-phenylcarbamoyl-heptanoylaminooxy)-tetrahydro-pyran-2-carboxylic acid methyl ester