2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

Base Information

• Chemical Name: 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal
• CAS No.: 945224-35-1
• Molecular Formula: C₄₅H₅₄O₇S₂
• Molecular Weight: 771.052
• Mol file: 945224-35-1.mol

Synonyms:2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

Chemical Property of 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

There total 8 articles about 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose 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%

2-O-pivaloyl-3-O-benzyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal (945224-34-0) + levulinic acid (123-76-2) → 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal (945224-35-1)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1002/chem.200700141

Reference yield:

3-O-benzyl-D-xylose di(ethylthio)acetal (945224-30-6) → 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal (945224-35-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / pTsOH / 12 h / 20 °C

2: 100 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

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

4: 90 percent / pyridine / 24 h / 20 °C

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

With pyridine; dmap; toluene-4-sulfonic acid; acetic acid; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1002/chem.200700141

Reference yield:

3-O-benzyl-4,5-O-isopropylidene-D-xylose di(ethylthio)acetal (945224-31-7) → 2-O-pivaloyl-3-O-benzyl-4-O-levulinoyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal (945224-35-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 90 percent / pyridine / 24 h / 20 °C

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

With pyridine; dmap; acetic acid; diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1002/chem.200700141

upstream raw materials:

2-O-pivaloyl-3-O-benzyl-5-O-triphenylmethyl-D-xylose di(ethylthio)acetal

levulinic acid

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

3-O-benzyl-4,5-O-isopropylidene-D-xylose di(ethylthio)acetal

Downstream raw materials:

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

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6R)-6-[5-(Benzyl-benzyloxycarbonyl-amino)-pentyloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxy)-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

C₂₆H₃₈O₇S₂

Refernces