2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 912567-61-4
• Molecular Formula: C₃₅H₄₀O₁₀
• Molecular Weight: 620.697

Synonyms:2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Chemical Property of 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

There total 9 articles about 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-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: 60.0%

Acetic acid (3R,4R,5R)-2-acetoxy-5-benzyl-4-((2R,3R,4S,5R,6R)-4,5-diacetoxy-3-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester (885671-70-5) → 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside (912567-61-4) + (2R,3R,4S)-4-acetoxy-2-benzyl-tetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1021/jm060310d

Reference yield:

2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside (518332-41-7) → 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside (912567-61-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 93 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: aq. TFA / 20 °C

6.1: Et₃N; DMAP / acetonitrile / 20 °C

7.1: 60 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.33 h / 0 °C

With triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation;

DOI:10.1021/jm060310d

Reference yield:

1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside (196868-07-2) → 2-benzyl-4-hydroxytetrahydrofuran-3-yl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside (912567-61-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 78 percent / 2,6-di-tert-butyl-4-methylpyridine / diethyl ether / 8 h / -78 °C

2.1: 82 percent / TBAF / tetrahydrofuran / 20 °C

3.1: tetrahydrofuran / 20 °C

4.1: PhOCSCl; DMAP / acetonitrile / 20 °C

4.2: 93 percent / Bu₃SnH; AIBN / toluene / Heating

5.1: aq. TFA / 20 °C

6.1: Et₃N; DMAP / acetonitrile / 20 °C

7.1: 60 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.33 h / 0 °C

With triethylsilane; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 3.1: Moffatt oxidation / 5.2: Barton deoxygenation;

DOI:10.1021/jm060310d

upstream raw materials:

Acetic acid (3R,4R,5R)-2-acetoxy-5-benzyl-4-((2R,3R,4S,5R,6R)-4,5-diacetoxy-3-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-phenylsulfinyl-β-D-glucopyranoside

5-deoxy-3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-5-phenyl-α-D-glucopyranosyl]-1,2-O-isopropylidene-α-D-ribofuranose

3-O-[2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-α-D-glucopyranosyl]-1,2-O-isopropylidene-5-phenyl-α-D-ribofuranose

Downstream raw materials:

C₅₅H₅₇O₁₇P₃

2-benzyl-4-tetrahydrofuran-3-yl 2,6-di-O-benzyl-α-D-glucopyranoside

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