5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol

Base Information

• Chemical Name: 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol
• CAS No.: 853734-15-3
• Molecular Formula: C₃₃H₄₂O₁₃
• Molecular Weight: 646.689
• Mol file: 853734-15-3.mol

Synonyms:5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol

Chemical Property of 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol

There total 7 articles about 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol 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%

5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-1-O-tert-butyldimethylsilyl-L-arabitol (853734-14-2) → 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol (853734-15-3)

Guidance literature:

With acetic acid; at 45 ℃; for 4h;

DOI:10.1021/ol050324y

Reference yield:

3,6-di-O-benzyl-L-arabinopyranose → 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol (853734-15-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / NaBH₄ / ethanol / 5 h / 20 °C

2: 77 percent / TsOH; 3 Angstroem molecular sieves / 4 h / 20 °C

3: 77 percent / pyridine / 20 °C

4: aq. AcOH / 2 h / 40 °C

5: 139 mg / imidazole / dimethylformamide / 2 h / 0 °C

6: 88 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

7: 82 percent / aq. AcOH / 4 h / 45 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; toluene-4-sulfonic acid; acetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050324y

Reference yield:

3,4-di-O-benzyl-1,2-O-isopropylidene-L-arabitol (853734-11-9) → 5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabitol (853734-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 77 percent / pyridine / 20 °C

2: aq. AcOH / 2 h / 40 °C

3: 139 mg / imidazole / dimethylformamide / 2 h / 0 °C

4: 88 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / 0 °C

5: 82 percent / aq. AcOH / 4 h / 45 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050324y

upstream raw materials:

5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-1-O-tert-butyldimethylsilyl-L-arabitol

3,4-di-O-benzyl-1,2-O-isopropylidene-L-arabitol

3,4-di-O-benzyl-L-arabitol

5-O-acetyl-3,4-di-O-benzyl-1,2-O-isopropylidene-L-arabitol

Downstream raw materials:

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-5-O-acetyl-3,4-di-O-benzyl-L-arabinose(open)-[(1R)->3,23]-28-benzyl hederagenate

methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-5-O-acetyl-3,4-di-O-benzylarabinose(open)-[1(R)->4,6]-2,3-di-O-benzyl-α-glucopyranoside

5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabinose