Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester
• CAS No.: 327603-93-0
• Molecular Formula: C₂₇H₃₄O₈S₃
• Molecular Weight: 582.76

Synonyms:Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester

Chemical Property of Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester

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Technology Process of Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester

There total 3 articles about Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl 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: 99.0%

phenyl 3-O-(methylthio)carbonyl-4-O-methyl-2-S-phenyl-2,6-di-deoxy-β-L-glucopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (327603-72-5) → Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester (327603-93-0)

Guidance literature:

With 80percent AcOH; at 50 ℃; for 8h;

DOI:10.1021/ol006894+

Reference yield:

phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside (327603-45-2) → Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester (327603-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / tetrahydrofuran / 2 h / Heating

2: 90 percent / 4 Angstroem molecular sieves; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 20 °C

3: 99 percent / 80percent AcOH / 8 h / 50 °C

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol006894+

Reference yield:

phenyl 4-O-methyl-2,3-O-thionocarbonyl-1-thio-α-L-rhamnopyranoside (327603-48-5) → Thiocarbonic acid O-[(2R,3S,4R,5S,6S)-2-((2S,3R,4S,5R,6S)-4,5-dihydroxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-5-methoxy-6-methyl-3-phenylsulfanyl-tetrahydro-pyran-4-yl] ester S-methyl ester (327603-93-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 4 Angstroem molecular sieves; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 20 °C

2: 99 percent / 80percent AcOH / 8 h / 50 °C

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; In dichloromethane;

DOI:10.1021/ol006894+

upstream raw materials:

phenyl 3-O-(methylthio)carbonyl-4-O-methyl-2-S-phenyl-2,6-di-deoxy-β-L-glucopyranosyl-(1->4)-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

phenyl 4-O-methyl-1-thio-α-L-rhamnopyranoside

phenyl 4-O-methyl-2,3-O-thionocarbonyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

phenyl 3-O-(methylthio)carbonyl-4-O-methyl-2-S-phenyl-2,6-di-deoxy-β-L-glucopyranosyl-(1->4)-2,3-O-thionocarbonyl-1-thio-α-L-rhamnopyranoside

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