95581-07-0

Basic information

• Product Name: 2,3,4-TRI-O-ACETYL-BETA-L-FUCOPYRANOSYL AZIDE
• Synonyms: 2,3,4-TRI-O-ACETYL-BETA-L-FUCOPYRANOSYL AZIDE;2,3,4-Tri-O-acetyl-b-L-fucopyranosylazide;2,3,4-TRI-O-ACETYL-SS-L-FUCOPYRANOSYL AZIDE;2,3,4-Tri-O-acetyl-beta-L-fucopyranosyl azide,99%
• CAS NO: 95581-07-0
• Molecular Formula: C₁₂H₁₇N₃O₇
• Molecular Weight: 315.28
• Mol File: 95581-07-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 125°C
• Boiling Point: 454.84°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3266 (rough estimate)
• Refractive Index: 1.5290 (estimate)
• CAS DataBase Reference: 2,3,4-TRI-O-ACETYL-BETA-L-FUCOPYRANOSYL AZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-TRI-O-ACETYL-BETA-L-FUCOPYRANOSYL AZIDE(95581-07-0)
• EPA Substance Registry System: 2,3,4-TRI-O-ACETYL-BETA-L-FUCOPYRANOSYL AZIDE(95581-07-0)

Safety Data

• Hazardous Substances Data: 95581-07-0(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

InChI:InChI=1/C12H17N3O7/c1-5-9(20-6(2)16)10(21-7(3)17)11(22-8(4)18)12(19-5)14-15-13/h5,9-12H,1-4H3/t5-,9+,10+,11-,12+/m0/s1

Upstream product

• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 73-34-7 6-deoxy-L-galactose 
• 108-24-7 acetic anhydride 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-β-L-fucopyranose 
• 2438-80-4 L-Fucose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 28915-80-2 2,3,4-tri-O-acetyl-L-fucopyranose 
• 64913-16-2 L-fucose tetraacetate 
• 128473-04-1 diphenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl phosphate 

Downstream Products

• 1029899-27-1 (3R)-1-[1-(methoxycarbonyl)isopropyl]-3-(2-nitrobenzenesulfonamino)-3-[1-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1,2,3-triazol-4-ylmethyl]-azetidin-2-one 
• 1329602-73-4 C₂₇H₃₄N₂O₁₀ 
• 1433555-02-2 1-[2-(benzyloxycarbonyl)-2-propyl]-1'-(2,3,4-tri-O-acetyl-β-L-fucosyl)-4,4'-methylenebis(1H-1,2,3-triazole) 
• 1433554-88-1 C₃₀H₃₉N₅O₁₁ 
• 1361486-11-4 4-phenyl-1-(2',3',4'-tri-O-acetyl-β-L-fucopyranosyl)-1,2,3-triazole 
• 138892-02-1 N-Formyl-N-(2,3,4-tri-O-pivaloyl-β-L-fucopyranosyl)-L-(4-chlorophenyl)glycine N'-tert-butylamide 
• 205253-03-8 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-[(S)-2-((R)-2-benzyloxycarbonylamino-propionylamino)-4-carbamoyl-butyrylamino]-6-methyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Synthesis of biurets: Via TMSNCO addition to 1-aminosugars: Application in the de novo synthesis of dC oxidation products

The reaction between 1-aminosugars and trimethylisocyanate (TMSNCO) was optimised as a one-step synthetic strategy for the synthesis of sugar biurets. This protocol was successfully applied to a number of 1-aminosugars, which exclusively provided the corresponding biurets in 67-99% yields. The new methodology was applied in the de novo synthesis of N1-(2-deoxy-α/β-d-erythro-pentofuranosyl)biuret (dfBU) and N1-(2-deoxy-α/β-d-erythro-pentopyranosyl)biuret (dpBU), two known DNA lesions arising from the hydroxyl radical induced decomposition of 2′-deoxycytidine (dCyd).

AuBr3-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr3 in good to excellent yields. The method is applicable to a wide range of easily accessible per-Oacetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1-3 h at room temperature, the per-O-benzoylated disaccharides needed 2-3 h of heating at 55°C.

Sugara-oligoamides: Synthesis of DNA minor groove binders

Sugar-oligoamides have been designed and synthesized as structurally simple carbohydrate-based ligands to study carbohydratea-minor groove DNA interactions. Here we report an efficient solution-phase synthetic strategy to obtain two broad families of sugara-oligoamides. The first type, structure vector A (-Py[Me]-γ-Py-Ind), has a methyl group present as a substituent on the nitrogen of pyrrole B, connected to the C terminal of the oligoamide fragment. The second type, structure vector B (-Py[(CH2) 11OH]-γ-Py-Ind), has an alkyl chain present on the nitrogen of pyrrole B connected to the C terminal of the oligoamide fragment and has been designed to access to di-and multivalent sugara-oligoamides. By using sequential DIPC/HOBt coupling reactions, the oligoamide fragment-Py[R]-γ-Py-Ind has been constructed. The last coupling reaction between the anomeric amino sugar and the oligoamide fragment was carried out by activating the acid derivative as a BtO-ester, which has been performed by using TFFH. The isolated esters (BtO-Py[R]-γ-Py-Ind) were coupled with selected amino sugars using DIEA in DMF. The synthesis of two different selective model vectors (vector A (1) and vector B (2)) and two types of water-soluble sugara-oligoamide ligands, with vector A structure (compounds 3a-7) and with vector B structure (compound 8), was carried out.