Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

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Chemical Name:Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester
CAS No.:78462-63-2
Molecular Formula:C₃₄H₃₆O₈S
Molecular Weight:604.721
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

There total 7 articles about Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-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: 86.0%

: 76-83-5
trityl chloride

: 78462-62-1
Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-2-hydroxymethyl-5,6-dimethoxy-tetrahydro-pyran-4-yl ester

: 78462-63-2
Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: at 70 ℃;
DOI:10.1246/cl.1981.457

Reference yield:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 78462-63-2
Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 47.1 percent / pyridinium p-toluenesulfonate / acetone; dimethylformamide / 36 h / 5 °C

2: 53.2 g / CH₂Cl₂; pyridine / 60 h

3: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

4: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

5: 86 percent / pyridine / 1.5 h / 70 °C

With Dowex 50W (H+); sodium hydride; pyridinium p-toluenesulfonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja00323a032

Reference yield:

: 63167-67-9
methyl 4,6-O-isopropylidene-α-D-mannopyranoside

: 78462-63-2
Toluene-4-sulfonic acid (2R,3R,4S,5S,6S)-3-hydroxy-5,6-dimethoxy-2-trityloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 53.2 g / CH₂Cl₂; pyridine / 60 h

2: 60 percent / NaH / tetrahydrofuran / 1.5 h / Ambient temperature

3: 100 percent / Dowex 50W (H+) / methanol / 3.5 h / Ambient temperature

4: 86 percent / pyridine / 1.5 h / 70 °C

With Dowex 50W (H+); sodium hydride; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1021/ja00323a032