(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol
CAS No.:1358580-57-0
Molecular Formula:C₂₂H₂₅ClO₇
Molecular Weight:436.889
Hs Code.:

Synonyms:(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

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Chemical Property of (2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

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Technology Process of (2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

There total 6 articles about (2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-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: 46.7%

: 75-75-2,98527-29-8
methanesulfonic acid

: 1358580-56-9
5-[(5-bromo-2-chloro-phenyl)methyl]-2,3-dihydrobenzofuran

: 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

: 1358580-57-0
(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Guidance literature:: 5-[(5-bromo-2-chloro-phenyl)methyl]-2,3-dihydrobenzofuran; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 1h;

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 3h;

methanesulfonic acid; In tetrahydrofuran; methanol; hexane; toluene; for 16h;

Reference yield:

: 1096875-61-4
(5-bromo-2-chloro-phenyl)-(2,3-dihydrobenzofuran-5-yl)methanone

: 1358580-57-0
(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 0 °C

2.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h

3.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C

3.2: 3 h / -78 °C

3.3: 16 h

With methanol; triethylsilane; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; toluene;

Reference yield:

: 496-16-2
2.3-dihydrobenzofuran

: 1358580-57-0
(2S,3R,4S,5S,6R)-2-[4-chloro-3-(2,3-dihydrobenzofuran-5-ylmethyl)phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: aluminum (III) chloride / dichloromethane / 2 h

2.1: sodium tetrahydroborate; methanol / tetrahydrofuran / 0.5 h / 0 °C

3.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 16 h

4.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 1 h / -78 °C

4.2: 3 h / -78 °C

4.3: 16 h

With methanol; triethylsilane; aluminum (III) chloride; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; toluene;