(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

Base Information

Chemical Name:(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol
CAS No.:1443119-70-7
Molecular Formula:C₂₁H₂₄BrClO₉
Molecular Weight:535.773
Hs Code.:

Synonyms:(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

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Chemical Property of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

Chemical Property:

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Technology Process of (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

There total 6 articles about (1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol 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: 96.0%

: 1443119-69-4
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(2-chloro-5-methylphenyl)-D-glucitol

: 1443119-70-7
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

Guidance literature:: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 1.5h; Reflux;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: 57310-39-1
2-bromo-1-chloro-4-methylbenzene

: 1443119-70-7
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 1 h / -78 °C

2.1: boron trifluoride diethyl etherate; chlorotriisopropylsilane / acetonitrile / 2 h / -40 °C

3.1: boron tribromide / dichloromethane / 1 h / -78 °C

4.1: pyridine / 20 °C

5.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1.5 h / Reflux

With N-Bromosuccinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); chlorotriisopropylsilane; boron trifluoride diethyl etherate; boron tribromide; In tetrahydrofuran; pyridine; tetrachloromethane; hexane; dichloromethane; acetonitrile;
DOI:10.1016/j.bmc.2013.03.067

Reference yield:

: 1443119-68-3
(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-(2-chloro-5-methylphenyl)-D-glucitol

: 1443119-70-7
(1S)-1,5-anhydro-2,3,4,6-tetra-O-acetyl-1-(5-(bromomethyl)-2-chlorophenyl)-D-glucitol

Guidance literature:: Multi-step reaction with 3 steps

1: boron tribromide / dichloromethane / 1 h / -78 °C

2: pyridine / 20 °C

3: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1.5 h / Reflux

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); boron tribromide; In pyridine; tetrachloromethane; dichloromethane;
DOI:10.1016/j.bmc.2013.03.067