2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

Base Information

Chemical Name:2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal
CAS No.:218449-12-8
Molecular Formula:C₁₅H₂₀O₆S
Molecular Weight:328.386
Hs Code.:

Synonyms:2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

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Chemical Property of 2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

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Technology Process of 2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

There total 11 articles about 2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal 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: 80.0%

: 98-59-9
p-toluenesulfonyl chloride

: 208394-56-3
2,5-anhydro-3,6-dideoxy-L-xylo-hexose ethylene acetal

: 218449-12-8
2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

Guidance literature:: With pyridine; for 48h; Ambient temperature;
DOI:10.1135/cccc19981522

Reference yield:

: 218449-02-6
2,5-anhydro-3-O-methanesulfonyl-L-idose ethylene acetal

: 218449-12-8
2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

Guidance literature:: Multi-step reaction with 7 steps

1: 87 percent / toluene-4-sulfonic acid / 24 h / 20 °C

2: 76 percent / Bu₄NF / acetonitrile / 48 h / Heating

3: 94 percent / H₂ / PtO₂ / ethanol / 24 h / 20 °C

4: 79 percent / CF₃COOH / methanol / 0.5 h / 20 °C

5: 80 percent / pyridine / 144 h / -28 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

7: 80 percent / pyridine / 48 h / 20 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; acetonitrile; 1: cyclocondensation / 2: Elimination / 3: Catalytic hydrogenation / 4: Hydrolysis / 5: Tosylation / 6: Reduction / 7: Tosylation;
DOI:10.1016/S0040-4020(00)00482-8

Reference yield:

: 208394-49-4
2,5-anhydro-3-O-p-toluenesulfonyl-L-idose ethylene acetal

: 218449-12-8
2,5-anhydro-3,6-dideoxy-4-O-p-toluenesulfonyl-L-xylo-hexose ethylene acetal

Guidance literature:: Multi-step reaction with 7 steps

1: 86 percent / toluene-4-sulfonic acid / dimethylformamide / 24 h / 70 °C

2: 86 percent / Bu₄NF / acetonitrile / 24 h / Heating

3: H₂ / Pd/C / ethanol / 4 h / 20 °C

4: 0.45 percent / H₂; glacial acetic acid / Pd/C / ethanol / 12 h / 20 °C

5: 80 percent / pyridine / 144 h / -28 °C

6: 90 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

7: 80 percent / pyridine / 48 h / 20 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile; 1: cyclocondensation / 2: Elimination / 3: Catalytic hydrogenation / 4: Catalytic hydrogenation / 5: Tosylation / 6: Reduction / 7: Tosylation;
DOI:10.1016/S0040-4020(00)00482-8