144985-19-3

Basic information

• Product Name: 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE
• Synonyms: 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE;4-Methoxyphenyl3-O-allyl-b-D-galactopyranoside;4-Methoxyphenyl 3-O-Allyl-β-D-galactopyranoside;4-Methoxyphenyl 3-O-Allyl-&beta
• CAS NO: 144985-19-3
• Molecular Formula: C₁₆H₂₂O₇
• Molecular Weight: 326.34
• Product Categories: Biochemistry;Galactose;Glycosides;Sugars
• Mol File: 144985-19-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 141.0 to 145.0 °C
• Boiling Point: 538.932oC at 760 mmHg
• Flash Point: 279.736oC
• Appearance: /
• Density: 1.305g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: Freezer
• Solubility: slightly sol. in Methanol
• CAS DataBase Reference: 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE(144985-19-3)
• EPA Substance Registry System: 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE(144985-19-3)

Safety Data

• Hazardous Substances Data: 144985-19-3(Hazardous Substances Data)

Usage

Description

4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE is a white to off-white powder or crystal, which is a compound used in the synthesis of various chemical products. It is particularly known for its role in the creation of a versatile neuraminic acid C-disaccharide precursor, which is essential for the synthesis of C-glycoside analogs of gangliosides.

Uses

Used in Pharmaceutical Industry:
4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE is used as a reagent for the synthesis of a versatile neuraminic acid C-disaccharide precursor. This precursor is crucial in the production of C-glycoside analogs of gangliosides, which are significant components in the field of pharmaceuticals. The compound plays a vital role in the development of new drugs and therapies targeting various medical conditions.
Used in Chemical Research:
In the realm of chemical research, 4-METHOXYPHENYL 3-O-ALLYL-BETA-D-GALACTOPYRANOSIDE serves as a valuable compound for the synthesis of complex molecules and the exploration of novel chemical reactions. Its unique structure allows researchers to investigate its properties and potential applications in various chemical processes, contributing to the advancement of scientific knowledge in this field.

InChI:InChI=1/C16H22O7/c1-3-8-21-15-13(18)12(9-17)23-16(14(15)19)22-11-6-4-10(20-2)5-7-11/h3-7,12-19H,1,8-9H2,2H3/t12-,13+,14-,15+,16-/m1/s1

Upstream product

• 106-95-6 allyl bromide 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 2872-65-3 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 150-76-5 4-methoxy-phenol 
• 4163-60-4 β-D-galactose peracetate 

Downstream Products

• 400091-05-6 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 247027-78-7 p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 343254-39-7 4-methoxyphenyl 2,4,6-O-tri-O-acetyl-3-O-allyl-β-D-galactopyranoside 
• 400091-03-4 4-methoxyphenyl 3-O-allyl-6-O-benzyl-β-D-galactopyranoside 
• 400091-02-3 4-methoxyphenyl 3,6-di-O-allyl-β-D-galactopyranoside 
• 488092-50-8 p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 
• 753500-16-2 4-methoxyphenyl 3-O-allyl-2,4-di-O-benzoyl-β-D-galactopyranoside 
• 753500-38-8 4-methoxyphenyl 3-O-allyl-2,4-di-O-benzoyl-6-O-trityl-β-D-galactopyranoside 
• 753500-28-6 4-methoxyphenyl 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-3-O-allyl-2,4-di-O-benzoyl-β-D-galactopyranoside 
• 753500-29-7 6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-3-O-allyl-2,4-di-O-benzoyl-α-D-galactopyranosyl trichloroacetamidate 
• 753500-17-3 4-methoxyphenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-3-O-allyl-2,4-di-O-benzoyl-β-D-galactopyranoside 
• 753500-18-4 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-3-O-allyl-2,4-di-O-benzoyl-α-D-galactopyranosyl trichloroacetamidate 
• 488092-52-0 p-methoxyphenyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside 
• 493027-41-1 3-O-allyl-2,4,6-tri-O-benzoyl-D-galactopyranosyl trichoroacetimidate 

Relevant articles and documents

Neighboring group participation in glycosylation reactions by 2,6-disubstituted 2-O-benzoyl groups: A mechanistic investigation

Variable yields and glycosylation stereoselectivity were obtained for NIS/TfOH-medi- ated reaction of 4-methoxyphenyl 2,4,6-tetra-O-acetyl-β-D- galactopyranoside and thiogalactosides bearing acetyl, benzoyl, 2,6-dimethoxylbenzoyl, 2,4,6-trimethylbenzoyl, or 2,6-dichlorobenzoyl groups at the 2-positions and acetyl at the remainder. X-ray structures of 4-methylphenyl 2,3,4,6-tetra-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D-galactopyr anoside and 4-methylphenyl 3,4-O-isopropylidene-2,6-di-O-(2,4,6-trimethylbenzoyl)-1-thio- β-D-galactopyranoside revealed slightly distorted 4C1 chair conformations. Variable temperature NMR revealed that activation of 4-methylphenyl 2,3,4,6-tetra-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D- galactopyranoside afforded only dioxolenium ion, whereas 4-methylphenyl 3,4,6-tri-O-acetyl-2-O-(2,4,6-trimethylbenzoyl)-1-thio-β-D- galactopyranoside gave a 1:1 mixture of dioxolenium ion and glycosyl triflate. However, the reaction intermediates formed from these deactivated donors do not influence the glycosylation stereoselectivity; instead, it is influenced by steric and electronic interactions at the transition states. Copyright Taylor & Francis Group, LLC.

A practical synthesis of β-D-GlcA-(1→3)-β-D-Gal-(1→3)-β-D-Gal-(1→4)-D- Xyl, a part of the common linkage region of a glycosaminoglycan

A practical synthesis of β-D-GlcA-(1→3)-β-D-Gal-(1→3)-β-D-Gal-(1→4)- β-D-Xyl-(1→OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,4,6- tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-β-D-xylopyranoside, followed by deallylation. The β-(1→3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranoside as the key synthon. The α-(1→3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation.

C-glycoside analogs and methods for their preparation and use

The invention provides versatile sialic acid C-glycoside precursors that are useful for preparing C-glycoside analogs of Gangliosides, peptides, and proteins, as well as synthetic intermediates useful for the preparation of the precursors, and synthetic m