Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate

Base Information

• Chemical Name: Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate
• CAS No.: 934591-76-1
• Molecular Formula: C25H29NO12S
• Molecular Weight: 567.571
• Mol file: 934591-76-1.mol

Synonyms:Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate;Methyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosylonate;Methyl 5-AcetaMido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-β-D-glycero-D-galacto-2-nonulopyranosylonate;Methyl 5-AcetaMido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate;(3aR,4R,6R,7aS)-3-Acetylhexahydro-2-oxo-6-(phenylthio)-4-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-4H-pyrano[3,4-d]oxazole-6-carboxylic acid methyl ester;Methyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-&beta

Chemical Property of Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate

Chemical Property:

• Melting Point: 150.0 to 154.0 °C
• Boiling Point: 658.0±55.0 °C(Predicted)
• PKA: -4.18±0.60(Predicted)
• PSA: 186.34000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: 1.53720
• Storage Temp.: 0-10°C
• Solubility.: soluble in Chloroform

Purity/Quality:

98% ^*data from raw suppliers

Methyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-beta-D-galacto-2-nonulopyranosylonate >96.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate

There total 2 articles about Methyl (Phenyl 5-Acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-beta-D-glycero-D-galacto-2-nonulopyranosid)onate 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: 82.0%

acetic anhydride (108-24-7) + 4-Nitrophenyl chloroformate (7693-46-1) + acetyl chloride (75-36-5) + (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (155155-64-9) → methyl (phenyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate (934591-76-1)

Guidance literature:

(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester; With methanesulfonic acid; In methanol; for 24h; Reflux; Inert atmosphere;

4-Nitrophenyl chloroformate; With sodium hydrogencarbonate; In methanol; water; acetonitrile; at 0 ℃; Inert atmosphere;

acetic anhydride; acetyl chloride; Further stages;

DOI:10.1039/c6ob01688j

Reference yield:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate (118977-25-6) → methyl (phenyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate (934591-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: MsOH / methanol / 24 h / Heating

1.2: 78 percent / NaHCO₃ / acetonitrile; H₂O / 3 h / 0 °C

2.1: pyridine / 20 °C

2.2: 92 percent / iPr₂NEt / CH₂Cl₂ / 1 h / 0 °C

With pyridine; methanesulfonic acid; In methanol;

DOI:10.1021/jo062431r

Reference yield: 100.0%

methyl (phenyl-5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate (934591-76-1) → methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galactonon-2-ulopyranoside)onate (221909-84-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1021/jo062431r

upstream raw materials:

methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate

acetic anhydride

4-Nitrophenyl chloroformate

acetyl chloride

Downstream raw materials:

methyl (phenyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galactonon-2-ulopyranoside)onate

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ylopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside