(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

Chemical Name:(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:1344028-09-6
Molecular Formula:C₂₁H₂₈O₅S
Molecular Weight:392.516
Hs Code.:

Synonyms:(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Chemical Property of (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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Technology Process of (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 7 articles about (2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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: 28.0%

: 1344027-78-6
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1344028-09-6
(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With methanol; sodium methylate; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.08.014

Reference yield:

: 1156807-53-2
(4-ethylphenyl)(3-methylthiophen-2-yl)methanone

: 1344028-09-6
(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

1.1: bromine; acetic acid / 20 °C / Inert atmosphere

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 20 °C / Inert atmosphere

3.1: trimethylsilylmethyllithium / tetrahydrofuran; pentane / 2 h / -50 - -40 °C / Inert atmosphere

3.2: 2 h / -78 - -50 °C / Inert atmosphere

4.1: potassium phosphate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / water; toluene / 100 °C / Inert atmosphere

5.1: methanol; sodium methylate / 2 h / 20 °C / Inert atmosphere

With methanol; triethylsilane; potassium phosphate; boron trifluoride diethyl etherate; bromine; sodium methylate; palladium diacetate; trimethylsilylmethyllithium; acetic acid; tricyclohexylphosphine tetrafluoroborate; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; pentane; 4.1: Suzuki type coupling;
DOI:10.1016/j.bmc.2011.08.014

Reference yield:

: 61341-26-2
3-methylthenoyl chloride

: 1344028-09-6
(2R,3R,4S,5S,6R)-2-(5-(4-ethylbenzyl)-3,4-dimethylthiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine / chloroform / 0 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: bromine; acetic acid / 20 °C / Inert atmosphere

4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 20 °C / Inert atmosphere

5.1: trimethylsilylmethyllithium / tetrahydrofuran; pentane / 2 h / -50 - -40 °C / Inert atmosphere

5.2: 2 h / -78 - -50 °C / Inert atmosphere

6.1: potassium phosphate; palladium diacetate; tricyclohexylphosphine tetrafluoroborate / water; toluene / 100 °C / Inert atmosphere

7.1: methanol; sodium methylate / 2 h / 20 °C / Inert atmosphere

With methanol; triethylsilane; potassium phosphate; boron trifluoride diethyl etherate; bromine; sodium methylate; palladium diacetate; trimethylsilylmethyllithium; acetic acid; triethylamine; tricyclohexylphosphine tetrafluoroborate; In tetrahydrofuran; dichloromethane; chloroform; water; toluene; acetonitrile; pentane; 6.1: Suzuki type coupling;
DOI:10.1016/j.bmc.2011.08.014