79120-81-3

Basic information

• Product Name: 1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF&
• Synonyms: 1,2,3,5-tetra-o-acetyl-α-l-arabinofuranose
• CAS NO: 79120-81-3
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.276
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 79120-81-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 385.6°C at 760 mmHg
• Flash Point: 168.5°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.76E-06mmHg at 25°C
• Refractive Index: 1.475
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF&(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF&(79120-81-3)
• EPA Substance Registry System: 1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF&(79120-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 79120-81-3(Hazardous Substances Data)

Usage

General Description

1,2,3,5-Tetra-O-acetyl-alpha-L-arabinofuranose, also known as tetraacetyl-L-arabinofuranose, is a chemical compound used in organic synthesis and as an intermediate in the preparation of various pharmaceuticals and other compounds. It is an acetylated form of L-arabinofuranose, a naturally occurring sugar. 1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF& is often used as a protecting group in carbohydrate chemistry, and it can be deprotected to reveal the hydroxyl groups of the sugar molecule for further functionalization. Additionally, it has been studied for its potential antiviral and anti-inflammatory properties.

InChI:InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12+,13+/m0/s1

Upstream product

• 5328-37-0 L-arabinose 
• 108-24-7 acetic anhydride 
• 87-72-9 L-(+)-arabinose 
• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 10323-20-3 D-Arabinose 
• 108-05-4 vinyl acetate 
• 32453-58-0 methyl-2,3,4-tri-O-acetyl-6-deoxy-β-L-glucopyranoside 
• 28697-53-2 D-arabinopyranose 
• 90244-44-3 methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside 
• 32453-59-1 (2R,3S,4R,5R)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1355330-54-9 1,2,3,5-tetra-O-tert-butyldimethylsilyl-α-L-arabinofuranose 
• 851367-08-3 methyl 2,3,6-tri-O-acetyl-5-deoxy-L-arabino-hexofuranoside 

Downstream Products

• 1027638-25-0 2-chloro-4-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 
• 1153940-80-7 methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-glucopyranoside 
• 1153940-88-5 methyl 2,3,4-tri-O-benzoyl-6-S-(2,3,5-tri-O-acetyl-α-L-arabinofuranosyl)-6-thio-α-D-galactoyranoside 
• 106824-96-8 2-β-D-ribofuranosyl-4-chloro-5-methoxycarbonyl-1,2,3-triazole 
• 328046-74-8 acetic acid 4-acetoxy-2-[2-(3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-(3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethoxy]-5-(1,2-diacetoxy-ethyl)-tetrahydro-furan-3-yl ester 
• 328046-75-9 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-2,3-di-O-benzyl-β-D-galactofuranoside 
• 328046-72-6 ethyl 5-O-(2',3',5'-tri-O-benzyl-α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside 
• 328046-70-4 Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[(R)-1-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-tetrahydro-furan-3-yl ester 
• 328046-71-5 ethyl 5-O-(α-D-arabinofuranosyl)-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-galactofuranoside 
• 328046-73-7 (R)-2-((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-2-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-ethoxy-tetrahydro-furan-2-yl)-ethanol 
• 461666-81-9 Acetic acid (2S,3S,4R,5S)-4-acetoxy-2-((2R,3R,4S,5S)-3,4-diacetoxy-5-acetoxymethyl-tetrahydro-furan-2-yloxymethyl)-5-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 461666-80-8 Acetic acid (2R,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(4-methoxy-phenoxy)-tetrahydro-furan-2-ylmethoxy]-tetrahydro-furan-3-yl ester 
• 461666-79-5 4'-methoxyphenyl α-L-arabinofuranoside 
• 402758-82-1 methyl 2-O-benzyl-α-D-arabinofuranoside 

Relevant articles and documents

A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction

A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the α-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.

Two-step synthesis of per-O-acetylfuranoses: Optimization and rationalization

A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate and N-acetylgalactosamine to give the corresponding peracetylated targets. The success of this procedure relied on the control of at least three parameters: (i) the tautomeric equilibrium of the starting unprotected oses, (ii) the steric hindrance of both targeted furanoses and silylating agent, and finally, (iii) the reactivity of each soft nucleophile during the protecting group interconversion.

Synthesis of a dimer of β-(1,4)-l-arabinosyl-(2 S,4 R)-4-hydroxyproline inspired by art v 1, the major allergen of mugwort

Nα-tert-Butoxycarbonyl-l-trans-4-hydroxyproline allyl ester (Boc-Hyp-OAll) was glycosylated with 2,3,5-tri-O-benzyl-l-arabinose p-cresylthioglycoside in 60% yield with 4:1 β:α stereoselectivity. Deprotection of N- and C-terminii independently gave a prolyl amine and prolyl carboxylate respectively that were coupled under standard conditions with 1-[bis-(dimethylamino)methylene]-1H-1,2,3-triazolo-[4,5,b]-pyridininium hexafluorophosphate 3-oxide (N-HATU) to give the dimer 1 in 46% yield. These results represent the first steps toward the production of homogeneous oligomers to determine the minimal epitope of the Art v 1 allergen.