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

Base Information

Chemical Name:(2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol
CAS No.:256327-55-6
Molecular Formula:C₂₀H₂₄O₅S
Molecular Weight:376.474
Hs Code.:

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

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

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

There total 6 articles about (2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol 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: 91.0%

: 256327-54-5
(2R,3S,4R,5S,6R)-3-(4-Methoxy-benzyloxy)-6-methyl-2-phenylsulfanyl-5-triisopropylsilanyloxy-tetrahydro-pyran-4-ol

: 256327-55-6
(2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H

Reference yield:

: 151669-25-9
Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

: 256327-55-6
(2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 5 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

5.1: 91 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; 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 / 5.1: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

: 126092-08-8
phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

: 256327-55-6
(2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine / 12 h / 0 - 25 °C

2.1: 36.65 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 90 percent / LAH / tetrahydrofuran / 6 h / 0 - 45 °C

4.1: 80 percent / TsOH; (CH₂OH)2 / methanol / 10 h / 25 °C

5.1: nBu₂SnO / toluene / 3 h / Heating

5.2: 83 percent / nBu₄NI / toluene / 3 h / 25 - 110 °C

6.1: 91 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Tosylation / 2.1: Etherification / 3.1: Reduction / 4.1: Ring cleavage / 5.1: Cyclization / 5.2: Ring cleavage / 6.1: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4