6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 332083-33-7
• Molecular Formula: C₅₆H₇₀O₂₂
• Molecular Weight: 1095.16

Synonyms:6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property of 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 5 articles about 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl 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: 34.0%

(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose (200712-66-9) + Allyl 2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranoside (332083-23-5) → 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (332083-33-7)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1002/1521-3765(20010216)7:4<858::AID-CHEM858>3.0.CO;2-N

Reference yield:

3-O-methyl-D-glucopyranose (3370-81-8) → 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (332083-33-7)

Guidance literature:

Multi-step reaction with 5 steps

1: TfOH / 2 h / 120 °C

2: 61.36 g / p-TsOH / toluene / 1 h / 80 °C

3: DMAP; NEt₃ / CH₂Cl₂ / 2 h

4: 0.95 g / Et₃SiH; TFAA; TFA / 1,2-dichloro-ethane / 4 h

5: 34 percent / TBDMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -20 °C

With triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; t-butyldimethylsiyl triflate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1002/1521-3765(20010216)7:4<858::AID-CHEM858>3.0.CO;2-N

Reference yield:

Allyl 4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside (332083-22-4) → 6-[4-acetoxy-6-(5-acetoxy-6-allyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yloxy)-2-acetoxymethyl-5-benzyloxy-tetrahydro-pyran-3-yloxy]-4,5-dimethoxy-3-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-carboxylic acid benzyl ester (332083-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP; NEt₃ / CH₂Cl₂ / 2 h

2: 0.95 g / Et₃SiH; TFAA; TFA / 1,2-dichloro-ethane / 4 h

3: 34 percent / TBDMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / -20 °C

With triethylsilane; dmap; 4 A molecular sieve; t-butyldimethylsiyl triflate; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1002/1521-3765(20010216)7:4<858::AID-CHEM858>3.0.CO;2-N

upstream raw materials:

(benzyl 4-O-levulinyl-2,3-di-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-acetyl-2-O-benzyl-1-O-trichloroacetimidoyl-D-glucopyranose

Allyl 2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranoside

3-O-methyl-D-glucopyranose

Allyl 4,6-O-benzylidene-3-O-methyl-α-D-glucopyranoside

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