methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate

Base Information

• Chemical Name: methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate
• CAS No.: 914955-17-2
• Molecular Formula: C₃₂H₃₄O₈S
• Molecular Weight: 578.683
• Mol file: 914955-17-2.mol

Synonyms:methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate

Chemical Property of methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate

There total 3 articles about methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate 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: 86.0%

methyl (phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate (914955-27-4) + levulinic anhydride (40608-06-8) → methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate (914955-17-2)

Guidance literature:

With pyridine; In 1,4-dioxane; at 20 ℃;

DOI:10.1021/ja064787q

Reference yield:

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranosiduronic acid (914955-24-1) → methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate (914955-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / K₂CO₃ / dimethylformamide / 10 h / 20 °C

2: 86 percent / pyridine / dioxane / 20 °C

With pyridine; potassium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ja064787q

Reference yield:

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside (449761-78-8) → methyl (phenyl 4-O-levulinoyl-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate (914955-17-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / TEMPO; BAIB / CH₂Cl₂; H₂O / 0 - 20 °C

2: 95 percent / K₂CO₃ / dimethylformamide / 10 h / 20 °C

3: 86 percent / pyridine / dioxane / 20 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; potassium carbonate; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja064787q

upstream raw materials:

methyl (phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside)uronate

levulinic anhydride

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranosiduronic acid

phenyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

C₅₀H₅₇N₃O₁₅

3-azidopropyl ((methyl 2,3-di-O-benzyl-4-O-(methyl 2,3-di-O-benzyl-β-D-mannopyranosyl)uronate)-β-D-mannopyranoside)uronate