(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1365769-39-6
• Molecular Formula: C₃₁H₃₂O₁₃
• Molecular Weight: 612.587
• Mol file: 1365769-39-6.mol

Synonyms:(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)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-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)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: 29.0%

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(p-tolyloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate + 2-hydroxy-4-(prop- 2-yn-1-yloxy)benzaldehyde (67268-54-6) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1365769-39-6)

Guidance literature:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(p-tolyloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate; With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 85 ℃; Inert atmosphere;

2-hydroxy-4-(prop- 2-yn-1-yloxy)benzaldehyde; With potassium carbonate; In acetonitrile; at 65 ℃; for 30h;

DOI:10.1021/ja3004045

Reference yield: 29.0%

2-hydroxy-4-(prop- 2-yn-1-yloxy)benzaldehyde (67268-54-6) + p-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (3520-64-7) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1365769-39-6)

Guidance literature:

p-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside; With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 85 ℃; Inert atmosphere;

2-hydroxy-4-(prop- 2-yn-1-yloxy)benzaldehyde; With potassium carbonate; In acetonitrile; at 65 ℃; for 30h;

DOI:10.1002/anie.201408560

Reference yield:

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate (74808-10-9,86520-63-0,92052-29-4,121238-27-5,127061-80-7,142831-80-9,87119-53-7) → (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((2-formyl-5-(prop-2-yn-1-yloxy)phenoxy)methyl)phenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1365769-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -42 °C / Inert atmosphere; Molecular sieve

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 85 °C / Inert atmosphere

2.2: 30 h / 65 °C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; In tetrachloromethane; dichloromethane;

DOI:10.1002/anie.201408560

upstream raw materials:

2-hydroxy-4-(prop- 2-yn-1-yloxy)benzaldehyde

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

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate

p-cresol

Downstream raw materials:

diethyl 2-(4-(prop-2-yn-1-yloxy)-2-((4-(((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)benzyl)oxy)benzylidene)malonate