dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

Base Information

Chemical Name:dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate
CAS No.:1454318-64-9
Molecular Formula:C₂₄H₂₈O₇S
Molecular Weight:460.548
Hs Code.:

Synonyms:dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

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Chemical Property of dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

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Technology Process of dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

There total 8 articles about dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate 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: 93.0%

: 1454318-50-3
(R)-2-(benzyloxymethyl)-3-((S)-p-tolylsulfinyl)-2,5-dihydrofuran

: 108-59-8
malonic acid dimethyl ester

: 1454318-64-9
dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

Guidance literature:: malonic acid dimethyl ester; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Inert atmosphere;

(R)-2-(benzyloxymethyl)-3-((S)-p-tolylsulfinyl)-2,5-dihydrofuran; In N,N-dimethyl-formamide; at 60 ℃; for 6h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.093

Reference yield:

: 1454318-37-6
(3S,4R,5R)-5-(benzyloxymethyl)-4-(p-tolylthio)-tetrahydrofuran-3-ol

: 1454318-64-9
dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

2.1: pyridine / 24.5 h / 0 - 4 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4.2: 6 h / 60 °C / Inert atmosphere

With pyridine; sodium periodate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 4.2: |Michael Addition;
DOI:10.1016/j.tet.2013.07.093

Reference yield:

: 1454318-36-5
(2S,3R,4R)-5-(benzyloxy)-3-(p-tolylthio)pentane-1,2,4-triol

: 1454318-64-9
dimethyl 2-((3R,4S,5R)-5-(benzyloxymethyl)-4-((R)-p-tolylsulfinyl)-tetrahydrofuran-3-yl)malonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: p-toluenesulfonyl chloride; pyridine / toluene / 72.5 h / 0 - 4 °C / Inert atmosphere

2.1: sodium periodate / methanol; water / 5 h / 20 °C / Inert atmosphere

3.1: pyridine / 24.5 h / 0 - 4 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5.2: 6 h / 60 °C / Inert atmosphere

With pyridine; sodium periodate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 5.2: |Michael Addition;
DOI:10.1016/j.tet.2013.07.093