2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate
• CAS No.: 1352447-39-2
• Molecular Formula: C₁₇H₂₄O₈S
• Molecular Weight: 388.439

Synonyms:2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Chemical Property of 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Chemical Property:

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Technology Process of 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

There total 7 articles about 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate 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:

2-(((3aR,4R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate (1352447-38-1) → 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate (1352447-39-2) + 2-(((3aR,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h; optical yield given as %de;

DOI:10.1016/j.tet.2011.10.063

Reference yield:

2,3-O-isopropylidene-β-D-ribofuranose (67814-68-0) → 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate (1352447-39-2) + 2-(((3aR,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

1.2: 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil

2.2: 12 h / 20 °C

3.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 20 °C

4.1: sodium periodate / dichloromethane; water / 3 h / 20 °C

5.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

5.2: Saturated solution

6.1: 1,4-diaza-bicyclo[2.2.2]octane; triethylamine / dichloromethane / 0.5 h / 20 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2011.10.063

Reference yield:

((3aR,4R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methanol (1352447-35-8) → 2-(((3aR,4R,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate (1352447-39-2) + 2-(((3aR,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil

1.2: 12 h / 20 °C

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 20 °C

3.1: sodium periodate / dichloromethane; water / 3 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C

4.2: Saturated solution

5.1: 1,4-diaza-bicyclo[2.2.2]octane; triethylamine / dichloromethane / 0.5 h / 20 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tet.2011.10.063

upstream raw materials:

((3aR,4R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methanol

(3aR,4R,6R,6aR)-4-(allyloxymethyl)-6-(4-methoxybenzyloxy)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

2-(((3aR,4R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methoxy)ethanol

2-(((3aR,4R,6R,6aR)-6-(4-methoxybenzyloxy)-2,2-dimethyltetrahydrofuro[3,4-d]-[1,3]dioxol-4-yl)methoxy)ethyl 4-methylbenzenesulfonate

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