(2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol
• CAS No.: 256327-54-5
• Molecular Formula: C₂₉H₄₄O₅SSi
• Molecular Weight: 532.817

Synonyms:(2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Chemical Property of (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

Chemical Property:

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Technology Process of (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

There total 6 articles about (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol 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: 83.0%

p-methoxybenzyl chloride (824-94-2) + (2R,3S,4R,5S,6R)-6-Methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-3,4-diol (256327-53-4) → (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (256327-54-5)

Guidance literature:

(2R,3S,4R,5S,6R)-6-Methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-3,4-diol; With di(n-butyl)tin oxide; In toluene; at 110 ℃; for 3h;

p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; In toluene; at 25 - 110 ℃;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (256327-54-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 36.65 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

2.1: 90 percent / LAH / tetrahydrofuran / 6 h / 0 - 45 °C

3.1: 80 percent / TsOH; (CH₂OH)2 / methanol / 10 h / 25 °C

4.1: nBu₂SnO / toluene / 3 h / Heating

4.2: 83 percent / nBu₄NI / toluene / 3 h / 25 - 110 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Ring cleavage / 4.1: Cyclization / 4.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-25-9) → (2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol (256327-54-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 36.65 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

2.1: 90 percent / LAH / tetrahydrofuran / 6 h / 0 - 45 °C

3.1: 80 percent / TsOH; (CH₂OH)2 / methanol / 10 h / 25 °C

4.1: nBu₂SnO / toluene / 3 h / Heating

4.2: 83 percent / nBu₄NI / toluene / 3 h / 25 - 110 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Ring cleavage / 4.1: Cyclization / 4.2: Ring cleavage;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

upstream raw materials:

p-methoxybenzyl chloride

(2R,3S,4R,5S,6R)-6-Methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-3,4-diol

triisopropylsilyl trifluoromethanesulfonate

Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

Downstream raw materials:

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

4-benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid 6-(4-benzyloxy-5-hydroxy-2-methyl-6-phenylselanyl-tetrahydro-pyran-3-yloxy)-4-(5-methoxy-4,6-dimethyl-4-nitro-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-4-allyloxy-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yl ester

4-Benzyloxy-3,5-dichloro-2-methoxy-6-methyl-benzoic acid (2R,3R,4R,6S)-6-[(2R,3R,4S,5R)-5-acetoxy-4-benzyloxy-2-methyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yloxy]-2-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-3-yl ester

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