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

Base Information

Chemical Name:(2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-ethylbenzyl)thiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS No.:842133-31-7
Molecular Formula:C₁₉H₂₃ClO₅S
Molecular Weight:398.908
Hs Code.:

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

There total 10 articles about (2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-ethylbenzyl)thiophen-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: 92.0%

: 1547297-57-3
(4aR,6S,7S,8R,8aR)-2,2-di-tert-butyl-6-[5-chloro-4-(4-ethylbenzyl)-2-thienyl]-8-[(triisopropylsilyl)oxy]-hexahydropyrano[3,2-d][1,3,2]dioxasilin-7-ol

: 842133-31-7
(2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-ethylbenzyl)thiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 3h;
DOI:10.1248/cpb.c13-00407

Reference yield:

: 1547297-60-8
(5-bromo-2-chloro-3-thienyl)(4-ethylphenyl)methanol

: 842133-31-7
(2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-ethylbenzyl)thiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1 h / -78 - 20 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 4 h / Reflux

3.1: borane-THF / tetrahydrofuran / 0 °C

3.2: 0 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 60 °C

With triethylsilane; bis-triphenylphosphine-palladium(II) chloride; borane-THF; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water;
DOI:10.1248/cpb.c13-00407

Reference yield:

: 1057216-05-3
5-bromo-2-chloro-3-(4-ethylbenzyl)thiophene

: 842133-31-7
(2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-ethylbenzyl)thiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 4 h / Reflux

2.1: borane-THF / tetrahydrofuran / 0 °C

2.2: 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; borane-THF; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water;
DOI:10.1248/cpb.c13-00407