14315-82-3

Basic information

• Product Name: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside
• Synonyms: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside
• CAS NO: 14315-82-3
• Molecular Weight: 610.617
• Mol File: 14315-82-3.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside(14315-82-3)
• EPA Substance Registry System: methyl 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranoside(14315-82-3)

Safety Data

• Hazardous Substances Data: 14315-82-3(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 
• 51023-63-3 methyl-α,β-D-mannopyranoside 
• 97-30-3 methyl D-galactopyranoside 
• 67-56-1 methanol 
• 627466-84-6 2,3,4,6-tetra-O-benzoyl-D-galactose 
• 3396-99-4 methyl α-D-galactopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 569329-23-3 Ectyoceramide hexaacetate 
• 571194-37-1 Ectyoceramide 
• 65236-82-0 1,2-O-(α-methoxybenzylidene)-3,4,6-tri-O-benzoyl-β-D-mannopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Downstream Products

• 34234-44-1 methyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 101194-17-6 methyl 2,3,4-tri-O-benzoyl-α-D-galactopyranoside 
• 1263311-55-2 methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 42927-28-6 methyl 6-O-benzoyl-α-D-galactopyranoside 
• 3396-68-7 methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 
• 80245-08-5 methyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 
• 14315-85-6 methyl 3, 6-di-O-benzoyl-α-D-mannopyranoside 
• 2592-58-7 1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside 

Relevant articles and documents

Ectyoceramide, the first natural hexofuranosylceramide from the marine sponge Ectyoplasia ferox

Ectyoceramide (1a), a unique monoglycosylceramide with a galactose in the furanose form, was isolated from Ectyoplasia ferox, and its structure was determined by NMR spectroscopy, multiple tandem mass spectrometry, and chemical degradation. Ectyoceramide is the first example of a monohexofuranosylceramide and, more generally, the first natural glycosphingolipid with its first sugar in the furanose form.

Sulfated liposaccharides inspired by telomerase inhibitor axinelloside A

Sulfated liposaccharides are known inhibitors of telomerase and here we describe the synthesis of a series of sulfated liposaccharides inspired by the natural product axinelloside A, reported to act as an inhibitor of human telomerase. We established a robust and scalable synthetic route to galactosyl liposaccharides capitalizing on a series of regioselective acylation reactions with 2-decenoic acid and imidazolium sulfate esters.

Blurring the boundary between bio- and geohopanoids: Plakohopanoid, a C32 biohopanoid ester from Plakortis cf. lita

Plakohopanoid (3a), a new type of hopanoid derivative composed of a C 32 hopanoid acid ester linked to a mannosyl-myo-inositol, was isolated from the sponge Plakortis cf. lita as its peracetyl derivative 3b. The structure of 3b was determined by a combination of spectroscopic analysis and micro-scale chemical degradation. Even though plakohopanoid was isolated from a sponge, its component parts are clearly of bacterial origin, and its bacterial biosynthesis is very likely. Until now, C32 hopanoic acids have been considered to be geohopanoids, i.e., diagenetic products that are formed through abiotic degradation of the biohopanoids present in bacteria. The presence of 3a in a marine living organism shows that there is a biosynthetic pathway to C32 hopanoic acids, and these substances should therefore no longer with certainty be considered to be geohopanoids. Copyright

Methyl 1,2-orthoesters as useful glycosyl donors in glycosylation reactions: A comparison with n-pent-4-enyl 1,2-orthoesters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and -benzoates (R = Ph) can function as glycosyl donors - upon BF3·Et 2O activation in CH2Cl2 - in glycosylation reactions with monosaccharide acceptors to afford disaccharides in good yields. In the process, glycosylation is preferred to acid-catalyzed rearrangement leading to methyl mannopyranosides. Methyl 1,2-orthoesters can be also used in regioselective glycosylation protocols with monosaccharide diols, in which they display good regioselectivity. Copyright

Unexpected stereocontrolled access to 1α,1′β-disaccharides from methyl 1,2-ortho esters

Mannopyranose-derived methyl 1,2-orthoacetates (R = Me) and 1,2-orthobenzoates (R = Ph) undergo stereoselective formation of 1α,1′β-disaccharides, upon treatment with BF 3?Et2O in CH2Cl2, rather than the expected acid-catalyzed reaction leading to methyl glycosides by way of a rearrangement-glycosylation process of the liberated methanol.

Isolation of the β-galactosphingolipid coniferoside using a tumor cell proteome reverse affinity protocol

New approaches are vital to the development of marine natural products (MNP) as therapeutic leads. One of the more time consuming aspects of MNP research arises in the connection between structure and function. Here, we describe an isolation protocol that adapts tumor cell proteomes as a vehicle for MNP isolation therein uniting structural and functional analysis. Application of this method to extracts of the sponge Agelas conifera led to the isolation of a unique poly-hydroxybutyrated β-galactosphingolipid, coniferoside.

Synthesis and structure elucidation of benzoylated deoxyfluoropyranosides

Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful

Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase

Thiodisaccharides having β-d-Galf or α-l-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-d-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-

1 Hand 13C NMR data of methyl tetra-O-benzoyl-D- pyranosides in acetone-d6

Complete assignments of 1H- and 13C-NMR resonances of five methyl tetra-O-benzoyl-D-pyranosides based on 1H, 13C, 2D DQF-COSY, HMQC, HMBC and HSQC-TOCSY experiments have been performed. Copyright

Regioselective C-6 hydrolysis of methyl O-benzoyl-pyranosides catalysed by candida rugosa lipase

Hydrolysis of six methyl O-benzoyl-pyranosides has been investigated using Candida rugosa lipase in dioxane/buffer mixtures. The lipase catalysed the hydrolysis of all substrates in a regiospecific manner at C-6, The rate of reaction was dependent on pyra