127501-41-1

Basic information

• Product Name: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE
• Synonyms: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE;Ethyl 2,3,4-tri-O-acetyl-b-L-thiofucopyranoside;ethyl-2,3,4-triacetyl--L-thifucopyranoside;Ethyl 6-deoxy-1-thio-beta-L-galactopyranoside 2,3,4-triacetate;Ethyl 6-deoxy-1-thio-beta-L-galactopyranoside triacetate
• CAS NO: 127501-41-1
• Molecular Formula: C₁₄H₂₂O₇S
• Molecular Weight: 334.38528
• Mol File: 127501-41-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 78-79℃ (ethanol )
• Appearance: /
• CAS DataBase Reference: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(127501-41-1)
• EPA Substance Registry System: ETHYL 2,3,4-TRI-O-ACETYL-1-THIO-BETA-L-FUCOPYRANOSIDE(127501-41-1)

Safety Data

• Hazardous Substances Data: 127501-41-1(Hazardous Substances Data)

Upstream product

• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 75-08-1 ethanethiol 
• 108-24-7 acetic anhydride 
• 24332-96-5 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride 
• 811-51-8 sodium thioethylate 
• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 64913-16-2 L-fucose tetraacetate 
• 6696-41-9 alpha-L-fucose 
• 73-34-7 6-deoxy-L-galactose 
• 60-29-7 diethyl ether 
• 3615-37-0 D-Fucose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 13224-93-6 β-L-fucopyranose 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 

Downstream Products

• 129948-10-3 methyl 2-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 116391-14-1 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,4aR,6S,7R,8S,8aR)-7-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 25019-69-6 methyl 4-O-benzyl-α-L-rhamnopyranoside 
• 137438-95-0 Methyl 2-O-acetyl-4-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-α-L-rhamnopyranoside 
• 137439-12-4 C₆₀H₆₀O₂₂ 
• 135129-62-3 Methyl 3,4-di-O-benzoyl-2-O-(2,3,4-tri-O-benzoyl-α-L-fucopyranosyl)-α-L-rhamnopyranoside 
• 116546-90-8 Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside 
• 137171-20-1 Acetic acid (2R,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 190248-99-8 ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xylo-hexopyranoside 
• 152015-42-4 S-ethyl 3,4-O-isopropylidene-2-O-p-methoxybenzyl-1-thio-β-L-fucopyranoside 
• 138343-56-3 ethyl 2-O-benzyl-1-thio-β-L-fucopyranoside 
• 190248-98-7 ethyl 2,4-di-O-benzyl-1-thio-β-L-fucopyranoside 
• 138343-55-2 ethyl 2-O-benzyl-3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 
• 138343-58-5 ethyl 4-O-acetyl-2,3-di-O-benzyl-1-deoxy-1-thio-β-L-fucopyranoside 

Relevant articles and documents

A facile synthesis of armed and disarmed colitose thioglycosides

Ethyl 2,4-di-O-acetyl-3,6-dideoxy-1-thio-β-L-xylohexopyranoside (10) and ethyl 2,4-di-O-benzyl-3,6-dideoxy-1-thio-β-L-xyl0-hexopyranoside (12) were synthesized in 60% and 55% overall yield, respectively. Starting from α-L-fucose, sequential peracetylation

Effect of Anomeric Configuration on Stereocontrolled α-Glycosylation of l -Fucose

In this letter, we report an approach to the stereoselective α-glycosylation of l -fucose that is exemplified by effect of anomeric configuration. The neighboring group participation is not compatible with α-glycosylation of l -fucose, therefore the remote participation by 4- O -Bz was employed to control the formation of 1,2- cis -glycosidic bond. Furthermore, we found the anomeric configuration of fucose donor is crucial to stereoselectivity of the glycosylated products. The α/β-mixed products were generated by using β-anomeric donor while the glycosyl donor in α configuration yielded products in high α-selectivity possibly due to the distinct pathway to forming the key intermediates. This phenomenon supplies the basis for the synthesis of complicated natural carbohydrates containing fucose α-glycoside, such as fucoidans, fucosylated N -glycans, and fucosylated chondroitin sulfates, etc.

Chemical Synthesis of a Glycopeptide Derived from Skp1 for Probing Protein Specific Glycosylation

Skp1 is a cytoplasmic and nuclear protein, best known as an adaptor of the SCF family of E3-ubiquitin ligases that label proteins for their degradation. Skp1 in Dictyostelium is posttranslationally modified on a specific hydroxyproline (Hyp) residue by a pentasaccharide, which consists of a Fucα1,2-Galβ-1,3-GlcNAcα core, decorated with two α-linked Gal residues. A glycopeptide derived form Skp1 was prepared to characterize the α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal moieties, and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells. A strategy was developed for the synthesis of the core trisaccharide-Hyp based on the use of 2-naphthylmethyl (Nap) ethers as permanent protecting groups to allow late stage installation of the Hyp moiety. Tuning of glycosyl donor and acceptor reactivities was critical for achieving high yields and anomeric selectivities of glycosylations. The trisaccharide-Hyp moiety was employed for the preparation of the glycopeptide using microwave-assisted solid phase peptide synthesis. Enzyme kinetic studies revealed that trisaccharide-Hyp and trisaccharide-peptide are poorly recognized by AgtA, indicating the importance of context provided by the native Skp1 protein for engagement with the active site. The trisaccharide-peptide was a potent immunogen capable of generating a rabbit antiserum that was highly selective toward the trisaccharide isoform of full-length Skp1. Antibody tracking: A glycopeptide containing a trisaccharide-hydroxyproline moiety was synthesized to characterize the substrate requirements of α-galactosyltransferase (AgtA) that mediates the addition of the α-Gal residues to the glycan of the glycoprotein Skp1 and to develop antibodies suitable for tracking the trisaccharide isoform of Skp1 in cells.