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

Base Information

• Chemical Name: 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
• CAS No.: 853734-22-2
• Molecular Formula: C₅₄H₆₄O₁₈
• Molecular Weight: 1001.09
• Mol file: 853734-22-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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: 70.0%

5-O-acetyl-2-[O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)]-3,4-di-O-benzyl-L-arabinose (853734-16-4) + methyl 2,3-di-O-benzyl-α-D-glucopyranoside (17791-36-5) → 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 (853734-22-2)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol050324y

Reference yield:

3,6-di-O-benzyl-L-arabinopyranose → 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 (853734-22-2)

Guidance literature:

Multi-step reaction with 9 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

8: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

9: 70 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; In ethanol; dichloromethane; N,N-dimethyl-formamide; 8: Dess-Martin oxidation;

DOI:10.1021/ol050324y

Reference yield:

3,4-di-O-benzyl-1,2-O-isopropylidene-L-arabitol (853734-11-9) → 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 (853734-22-2)

Guidance literature:

Multi-step reaction with 7 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

6: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

7: 70 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / -78 - 20 °C

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dess-Martin periodane; acetic acid; In dichloromethane; N,N-dimethyl-formamide; 6: Dess-Martin oxidation;

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-L-arabinose

methyl 2,3-di-O-benzyl-α-D-glucopyranoside

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

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