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

• 75-08-1 ethanethiol 
• 64913-16-2 L-fucose tetraacetate 
• 60-29-7 diethyl ether 
• 3615-37-0 D-Fucose 
• 75247-29-9 (2R,3S,4R,5R,6S)-2-bromo-6-methyltetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 108-24-7 acetic anhydride 
• 24332-96-5 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl chloride 
• 811-51-8 sodium thioethylate 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 80483-13-2 2,3,4-tri-O-acetyl-L-fucopyranosyl bromide 
• 73-34-7 6-deoxy-L-galactose 
• 132799-10-1 ethyl 1-thio-α-L-fucopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 13224-93-6 β-L-fucopyranose 

Downstream Products

• 1192875-49-2 methyl 2-acetamido-3-O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 116872-15-2 Ethyl 2,3,4-tri-O-p-chlorobenzyl-1-thio-β-L-fucopyranoside 
• 180476-30-6 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl-1-trichloroacetoimidate 
• 180476-31-7 ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside 
• 116546-90-8 Ethyl 2,3,4-tri-O-benzoyl-1-thio-β-L-fucopyranoside 
• 138552-47-3 dibenzyl 2,3,4-tri-O-benzoyl-β-L-fucopyranosyl 1-phosphate 
• 16562-59-7 β-L-Fucopyranosyl phosphate 
• 212780-39-7 (2S,3R)-2-{(2S,3R)-4-Benzyloxy-2-[4-(bis-benzyloxy-phosphoryl)-butyrylamino]-3-hydroxy-butyrylamino}-3-((2R,3S,4R,5S,6S)-3-benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester 
• 212780-31-9 (2S,3R)-3-[(3aR,4S,6R,7S,7aR)-7-Benzyloxy-2-(4-hydroxymethyl-phenyl)-4-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester 
• 289634-87-3 (2S,3R)-3-((3aR,4S,6R,7S,7aR)-7-Benzyloxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester 
• 212780-30-8 (2S,3R)-3-((2R,3S,4R,5S,6S)-3-Benzyloxy-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester 
• 131545-02-3 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 260970-15-8 methyl 2-O-benzoyl-3-O-benzyl-4-deoxy-4-fluoro-α-L-rhamnopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

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.

Total synthesis of LewisX using a late-stage crystalline intermediate

Abstract Herein, we report on a highly efficient synthesis of a crystalline protected LewisX trisaccharide that was converted to LewisX following global deprotection. The trisaccharide was prepared in a highly convergent synthesis (seven steps, longest linear sequence) and in a 38% overall yield using a strategy that involved the regioselective glycosylation of a GlcNAc acceptor with a galactose thioglycoside donor, followed by fucosylation of the remaining free GlcNAc hydroxyl as key steps. The core trisaccharide also has the potential to be converted to other members of the Type-2 Lewis family of antigens due to the orthogonal nature of the protecting groups employed.