methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal

Base Information

• Chemical Name: methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal
• CAS No.: 945224-40-8
• Molecular Formula: C₃₄H₅₆O₉S₂Si
• Molecular Weight: 701.031
• Mol file: 945224-40-8.mol

Synonyms:methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal

Chemical Property of methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal

There total 7 articles about methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal 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: 100.0%

methyl 2-O-pivaloyl-3-O-benzyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal (945224-39-5) + levulinic acid (123-76-2) → methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal (945224-40-8)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/chem.200700141

Reference yield:

C20H30O4S2 (945224-38-4) → methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal (945224-40-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / MgBr₂*OEt₂ / toluene; CH₂Cl₂ / 6 h / -78 - 20 °C

2: 100 percent / 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 20 h / 20 °C

With dmap; magnesium bromide; diisopropyl-carbodiimide; In dichloromethane; toluene; 1: Mukaiyama aldol reaction;

DOI:10.1002/chem.200700141

Reference yield:

3-O-benzyl-4,5-O-isopropylidene-D-xylose di(ethylthio)acetal (945224-31-7) → methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal (945224-40-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

2: 100 percent / aq. acetic acid / 3 h / 50 °C

3: 82 percent / sodium periodate / H₂O; tetrahydrofuran / 2 h / 20 °C

4: 85 percent / MgBr₂*OEt₂ / toluene; CH₂Cl₂ / 6 h / -78 - 20 °C

5: 100 percent / 4-dimethylaminopyridine; N,N'-diisopropylcarbodiimide / CH₂Cl₂ / 20 h / 20 °C

With dmap; sodium periodate; acetic acid; magnesium bromide; diisopropyl-carbodiimide; In tetrahydrofuran; dichloromethane; water; toluene; 4: Mukaiyama aldol reaction;

DOI:10.1002/chem.200700141

upstream raw materials:

methyl 2-O-pivaloyl-3-O-benzyl-5-O-tert-butyldimethylsilyl-D-glucuronate di(ethylthio)acetal

levulinic acid

C₂₀H₃₀O₄S₂

3-O-benzyl-D-xylose di(ethylthio)acetal

Downstream raw materials:

methyl 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-D-glucuronate di(ethylthio)acetal

Refernces