(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
CAS No.:1414856-82-8
Molecular Formula:C₂₁H₂₆O₁₀
Molecular Weight:438.431
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Chemical Property of (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Technology Process of (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)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: 38.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0
2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride

: 1414856-82-8
(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: With nickel(II) bromide dimethoxyethane; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine; In acetonitrile; at 25 ℃; for 24h; diastereoselective reaction; Inert atmosphere; Sealed tube; Irradiation;
DOI:10.1002/adsc.202100343

Reference yield:

: 13139-86-1
4-methoxyphenyl magnesium bromide

: 13242-53-0
acetobromomannose

: 1414856-82-8
(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1414856-76-0
1-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)benzene

Guidance literature:: With cobalt(III) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Overall yield = 70 %; diastereoselective reaction;
DOI:10.1002/anie.201204786 DOI:10.1002/anie.201204786

Reference yield:

: C₂₀H₃₀N₂O₂Zn*Br₂Cl₂Mg₂

: 13242-53-0
acetobromomannose

: 1414856-82-8
(2R,3R,4R,5R,6R)-2-(acetoxymethyl)-6-(4-methoxyphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: With dichloro(1,2-{bis[3,5-bis(trimethylsilyl)pheny]phosphino-κP}benzene)iron(II); In tetrahydrofuran; at 0 ℃; for 18h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/jacs.7b03867