[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

Base Information

Chemical Name:[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate
CAS No.:1373347-09-1
Molecular Formula:C₂₁H₂₅BrO₁₀
Molecular Weight:517.327
Hs Code.:

Synonyms:[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

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Chemical Property of [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

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Technology Process of [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

There total 2 articles about [(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate 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: 77.0%

: 2362-12-1
4-Bromo-2-methylphenol

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 1373347-09-1
[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 45h; Inert atmosphere; Reflux;
DOI:10.1021/jm300165m

Reference yield:

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1373347-09-1
[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

Guidance literature:: Multi-step reaction with 2 steps

1: iron(III) chloride / 3 h / 20 °C

2: boron trifluoride diethyl etherate / dichloromethane / 45 h / Inert atmosphere; Reflux

With iron(III) chloride; boron trifluoride diethyl etherate; In dichloromethane;

Reference yield: 79.0%

: 1373347-09-1
[(2R,3S,4S,5R,6R)-4,5-diacetoxy-6-(acetoxymethyl)-2-(4-bromo-2-methyl-phenoxy)tetrahydropyran-3-yl] acetate

: 73183-34-3
bis(pinacol)diborane

: 2-methyl-4-[4‘,4‘,5’,5’-tetramethyl-1,3-dioxaborolan-2-yl]phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 80 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.6b00948