(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate
CAS No.:1344027-77-5
Molecular Formula:C₂₈H₃₃BrO₉S
Molecular Weight:625.535
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Chemical Property of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Technology Process of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 5 articles about (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 20.0%

: 1344027-76-4
2,3-dibromo-5-(4-ethylbenzyl)-4-methylthiophene

: 108-24-7
acetic anhydride

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1344027-77-5
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: 2,3-dibromo-5-(4-ethylbenzyl)-4-methylthiophene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; With trimethylsilylmethyllithium; In tetrahydrofuran; pentane; at -50 - -40 ℃; for 2h; Inert atmosphere;

With methanol; methanesulfonic acid; In tetrahydrofuran; at -78 - -50 ℃; for 2h; Inert atmosphere;

acetic anhydride; Further stages;
DOI:10.1016/j.bmc.2011.08.014

Reference yield:

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

: 1344027-77-5
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: Multi-step reaction with 3 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

With triethylsilane; boron trifluoride diethyl etherate; bromine; trimethylsilylmethyllithium; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile; pentane;
DOI:10.1016/j.bmc.2011.08.014

Reference yield:

: 61341-26-2
3-methylthenoyl chloride

: 1344027-77-5
(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromo-5-(4-ethylbenzyl)-4-methylthiophen-2-yl)-tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: Multi-step reaction with 5 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

With triethylsilane; boron trifluoride diethyl etherate; bromine; trimethylsilylmethyllithium; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile; pentane;
DOI:10.1016/j.bmc.2011.08.014