4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 202647-65-2
• Molecular Formula: C₆₃H₇₆O₁₈S
• Molecular Weight: 1153.35

Synonyms:4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester

There total 12 articles about 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-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: 68.0%

Phenyl 6-O-benzyl-2,3-di-O-methyl-1-thio-α-D-glucopyranoside (202647-64-1) + 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate (202647-51-6) → 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (202647-65-2)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -20 ℃; for 0.166667h;

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

Reference yield: 68.0%

Phenyl 6-O-benzyl-2,3-di-O-methyl-1-thio-α-D-glucopyranoside (202647-64-1) + 2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-D-glucopyranose trichloroacetimidate → 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (202647-65-2)

Guidance literature:

With 4 A molecular sieve; t-butyldimethylsiyl triflate; In dichloromethane; at -20 ℃; for 0.166667h;

DOI:10.1016/S0960-894X(99)00155-9

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4-oxo-pentanoic acid 6-[5-acetoxy-2-benzyloxymethyl-6-(2-benzyloxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-4-methoxy-tetrahydro-pyran-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-methoxy-tetrahydro-pyran-3-yl ester (202647-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1: CSA / acetonitrile / 1 h / 20 °C

2: 840 mg / NaH / toluene / 0.5 h / 20 °C

3: 80 percent / TFAA; TFA; Et₃SiH / 1,2-dichloro-ethane

4: 68 percent / TBDMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.17 h / -20 °C

With triethylsilane; 4 A molecular sieve; camphor-10-sulfonic acid; t-butyldimethylsiyl triflate; sodium hydride; trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile;

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

upstream raw materials:

Phenyl 6-O-benzyl-2,3-di-O-methyl-1-thio-α-D-glucopyranoside

2,6-Di-O-benzyl-4-O-levulinyl-3-O-methyl-α-D-glucopyranosyl-(1->4)-2-O-acetyl-6-O-benzyl-3-O-methyl-α-D-glucopyranose trichloroacetimidate

benzaldehyde dimethyl acetal

thiophenol

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