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

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(bromomethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1261966-06-6
• Molecular Formula: C₂₁H₂₅BrO₁₀
• Molecular Weight: 517.327
• Mol file: 1261966-06-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(bromomethyl)phenoxy)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: 91.0%

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (259684-23-6,105054-56-6) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(bromomethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1261966-06-6)

Guidance literature:

With phosphorus tribromide; In diethyl ether; at 0 ℃; for 2h;

DOI:10.1021/acsmedchemlett.6b00427

Reference yield:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(p-tolyloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(bromomethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1261966-06-6)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 85 ℃; Inert atmosphere;

DOI:10.1021/ja3004045

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-(bromomethyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1261966-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: caesium carbonate / N,N-dimethyl-formamide; tetrahydrofuran / 0.17 h

1.2: 22.5 h / 20 °C

2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 1 h / 0 °C

3.1: phosphorus tribromide / diethyl ether / 2 h / 0 °C

With phosphorus tribromide; caesium carbonate; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/acsmedchemlett.6b00427

upstream raw materials:

p-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside

p-cresol

β-D-galactose peracetate

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

Downstream raw materials:

(4-aminomethyl-phenyl)-β-D-galactopyranoside

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2,4-bis(allyloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(2S,3R,4S,5R,6R)-2-(4-((2,4-dihydroxyphenoxy)methyl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C₂₉H₃₀O₁₃