303127-81-3

Basic information

• Product Name: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE;4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-β-D-glucopyranoside;4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-β(4aR,6S,7R,8R,8aR)-8-(benzyloxy)-6-(4-methoxyphenoxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS NO: 303127-81-3
• Molecular Formula: C₂₇H₂₈O₇
• Molecular Weight: 464.51
• Product Categories: Biochemistry;Glucose;Glycosides;Sugars
• Mol File: 303127-81-3.mol

Chemical Properties

• Melting Point: 204.0 to 211.0 °C
• Boiling Point: 641.98°C at 760 mmHg
• Flash Point: 342.057°C
• Appearance: /
• Density: 1.307g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Storage Temp.: Freezer
• PKA: 12.50±0.70(Predicted)
• CAS DataBase Reference: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE(303127-81-3)
• EPA Substance Registry System: 4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE(303127-81-3)

Safety Data

• Hazardous Substances Data: 303127-81-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE is used as a building block for the synthesis of other complex organic molecules, contributing to the development of novel chemical compounds with diverse applications.
Used in Pharmaceutical Industry:
4-METHOXYPHENYL 3-O-BENZYL-4,6-O-BENZYLIDENE-BETA-D-GLUCOPYRANOSIDE is used as a potential source of biologically active compounds, which may exhibit interesting pharmacological properties. Further research and testing are required to explore its full potential in drug discovery and development.

InChI:InChI=1/C27H28O7/c1-29-20-12-14-21(15-13-20)32-27-23(28)25(30-16-18-8-4-2-5-9-18)24-22(33-27)17-31-26(34-24)19-10-6-3-7-11-19/h2-15,22-28H,16-17H2,1H3/t22-,23-,24-,25-,26-,27-/m1/s1

Upstream product

• 100-52-7 benzaldehyde 
• 303127-80-2 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 303127-79-9 4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside 
• 150-76-5 4-methoxy-phenol 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 1535966-47-2 C₂₈H₃₈O₇Sn 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 

Downstream Products

• 303127-82-4 4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 763129-80-2 p-methoxypheyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoroethylsulfonato-β-D-glucopyranoside 
• 765910-39-2 p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-2-O-pivaloyl-β-D-glucopyranoside 
• 765910-20-1 tert-butyldimethylsilyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 765910-19-8 p-methoxyphenyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 765910-40-5 tert-butyldimethylsilyl 3-O-benzyl-4,6-di-O-benzylidene-2-O-pivaloyl-β-D-glucopyranoside 
• 763129-82-4 p-methoxyphenyl 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-β-D-glucopyranoside 
• 763129-79-9 6-O-acetyl-3,4-O-benzyl-2-O-trifluoroethylsulfonato-1-O-trichloroacetimidoyl-α-D-glucopyranoside 
• 763129-88-0 p-methoxyphenyl (3-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-trifluoroethylsulfonato-β-D-glucopyranosyluryl)-(1-4)-2-azido-3-O-benzoyl-6-O-benzyl-2-deoxy-4-O-trifluoroethylsulfonato-β-D-galactopyranoside 
• 303127-84-6 Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate 
• 303127-83-5 4-Methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranoside 
• 303128-06-5 (2S,3S,4S,5R,6S)-5-Benzoyloxy-3,4-bis-benzyloxy-6-(4-methoxy-phenoxy)-tetrahydro-pyran-2-carboxylic acid 
• 303127-85-7 Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano 
• 303128-10-1 (2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid 

Relevant articles and documents

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Neighbouring group participation during glycosylation: Do 2-substituted ethyl ethers participate?

The development of new protecting groups that undergo neighbouring group participation (NGP) via six-membered ring intermediates to promote the formation of α-1,2-cis glycosidic linkages complements the established use of 5-ring NGP in terms of stereochem

Synthesis of two trisaccharides related to the hepatoprotective phenylethanoids leonoside e and F isolated from Leonurus japonicus Houtt

The chemical synthesis of two trisaccharides related to leonoside E and F is reported. The target oligosaccharides were prepared in the form of their p-methoxyphenyl glycosides using a common disaccharide acceptor. All reaction steps were high yielding (>80%) and the stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)3.

Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6

The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no α-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly α-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best α-glucosylating block for the primary acceptor, whereas the best α-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 C) even lower α-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the α-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N- phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors.2013 Elsevier Ltd. All rights reserved.

Synthesis of two trisaccharides related to the triterpenoid saponins isolated from Solanum lycocarpum

Chemical synthesis of two trisaccharides related to the triterpenoid saponins isolated from Solanum lycocarpum from commercially available D-Glc, D-Gal and L-Rha have been achieved by following concise and high-yielding route. The target trisaccharide 1 h

Toward the modular synthesis of glycosaminoglycans: Synthesis of hyaluronic acid disaccharide building blocks using a periodic acid oxidation

The synthesis of two differentially protected GluNAc-β(1→4)-GluA and GluA-β(1→3)-GluNAc disaccharide modules for the solid-phase assembly of hyaluronic acid are described. A periodic acid/chromium trioxide oxidation was the key transformation to facilitate access to the glucuronic acid moiety from glucose and should find wide application in the oxidation of primary alcohols.

Chemical synthesis of β-D-GlcpA(2SO4)-(1→3)-D-GalpNAc(6SO4), the disaccharide repeating unit of shark cartilage chondroitin sulfate D, and of its methyl β-D-glycoside derivative

The syntheses of sodium O-(disodium 2-O-sulfonato-β-D-glucopyranosyluronate)-(1→3)-2-acetamido-2-deoxy-6- O-sulfonato-D-galactopyranose 1, which represents a structural element of shark cartilage chondroitin sulfate D, and of its methyl β-D-glycoside derivative 2 are reported for the first time. The glucuronyl donor 10 is prepared in a straightforward manner from D-glucose, whereas the glycosyl acceptors 20 and 21 are obtained from known 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-1-O-trichloroacetimidoyl- α-D-glucopyranose through glycosylation with benzyl alcohol and methanol, respectively, and subsequent transformation into D-galacto synthons by selective inversion of configuration at C-4. Unexpected pyranose → furanose ring contraction as well as 3,6-anhydro-derivative formation in the D-galacto series are also reported. Stereocontrolled coupling of the imidate 10 with the alcohols 20 and 21 afforded the corresponding β-linked disaccharide derivatives 24 and 25, respectively, which are submitted to radical reduction of the N-trichloroacetyl groups, O-desilylation, saponification, O-sulfonation, and catalytic hydrogenation to provide the target molecules 1 and 2, respectively, in high yields. The Royal Society of Chemistry 2000.