2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose

Base Information

• Chemical Name: 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose
• CAS No.: 403731-56-6
• Molecular Formula: C₄₆H₅₂O₁₃
• Molecular Weight: 812.911

Synonyms:2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose

Chemical Property of 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose

There total 14 articles about 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose 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: 67.0%

p-methylanizole (104-93-8) + 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside (197644-83-0) → 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose (403731-56-6)

Guidance literature:

With silver trifluoroacetate; tin(IV) chloride; In chloroform; at 20 ℃; for 0.75h;

DOI:10.1002/1521-3765(20011119)7:22<4937::AID-CHEM4937>3.0.CO;2-G

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose (403731-56-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / TsOH / dimethylformamide; methanol / 2 h / 70 °C

2.1: 68 percent / NaCNBH₃; HCl; 3 Angstroem molecular sieves / tetrahydrofuran; diethyl ether / 0.08 h / 20 °C

3.1: DMSO; Ac₂O / 18 h / 20 °C

4.1: NaBH₄ / ethanol; H₂O / 1 h / 20 °C

5.1: 81 percent / ZnCl₂; AgClO₄; 4 Angstroem molecular sieves / dioxane; toluene / 22 h / 20 °C

6.1: 75 percent / acetic acid; water / ethane-1,2-diol / 0.25 h / Heating

7.1: 82 percent / pyridine / 20 h / 20 °C

8.1: AgCO₃CF₃; SnCl₄ / Heating

8.2: TMSOTf / 1,2-dichloro-ethane / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; 3 A molecular sieve; 4 A molecular sieve; AgCO₃CF₃; water; silver perchlorate; acetic anhydride; tin(IV) chloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; zinc(II) chloride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; ethylene glycol; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Oxidation / 4.1: Reduction / 5.1: Condensation / 6.1: Ring cleavage / 7.1: Acetylation / 8.1: Condensation / 8.2: Solvolysis;

DOI:10.1039/a909347h

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 2-O-acetyl-5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)-D-ribofuranose (403731-56-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / TsOH / dimethylformamide; methanol / 2 h / 70 °C

2.1: 68 percent / NaCNBH₃; HCl; 3 Angstroem molecular sieves / tetrahydrofuran; diethyl ether / 0.08 h / 20 °C

3.1: DMSO; Ac₂O / 18 h / 20 °C

4.1: NaBH₄ / ethanol; H₂O / 1 h / 20 °C

5.1: 81 percent / ZnCl₂; AgClO₄; 4 Angstroem molecular sieves / dioxane; toluene / 22 h / 20 °C

6.1: 75 percent / acetic acid; water / ethane-1,2-diol / 0.25 h / Heating

7.1: 82 percent / pyridine / 20 h / 20 °C

8.1: AgCO₃CF₃; SnCl₄ / Heating

8.2: TMSOTf / 1,2-dichloro-ethane / Heating

With pyridine; hydrogenchloride; sodium tetrahydroborate; 3 A molecular sieve; 4 A molecular sieve; AgCO₃CF₃; water; silver perchlorate; acetic anhydride; tin(IV) chloride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; zinc(II) chloride; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; ethylene glycol; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Ring cleavage / 3.1: Oxidation / 4.1: Reduction / 5.1: Condensation / 6.1: Ring cleavage / 7.1: Acetylation / 8.1: Condensation / 8.2: Solvolysis;

DOI:10.1039/a909347h

upstream raw materials:

p-methylanizole

1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside

3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-α-D-ribofuranose

5-O-benzyl-1-(4-methylanisol-2-yl)-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose

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