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

Base Information

• Chemical Name: 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
• CAS No.: 885671-70-5
• Molecular Formula: C₃₉H₄₄O₁₃
• Molecular Weight: 720.771

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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:

(2R,3S,4S,5R,6R)-6-((2R,3S,4R)-2-Benzyl-4,5-dihydroxy-tetrahydro-furan-3-yloxy)-5-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3,4-diol + acetic anhydride (108-24-7) → 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)

Guidance literature:

With dmap; triethylamine; In acetonitrile; at 20 ℃;

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) → 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)

Guidance literature:

Multi-step reaction with 7 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

With dmap; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; triethylamine; trifluoroacetic acid; phenylcarbonochloridothioate; In tetrahydrofuran; diethyl ether; 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) → 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)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1021/jm060310d

upstream raw materials:

acetic anhydride

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:

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

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

C₅₅H₅₇O₁₇P₃

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