43225-70-3

Basic information

• Product Name: 1,2,3,5-TETRA-O-ACETYL-ALPHA-D-ARABINOF&
• Synonyms: 1,2,3,5-tetra-o-acetyl-α-d-arabinofuranose;1-O,2-O,3-O,5-O-Tetraacetyl-α-D-arabinofuranose;Acetyl 2-O,3-O,5-O-triacetyl-α-D-arabinofuranoside;α-D-Arabinofuranose tetraacetate;a-D-Arabinofuranose, tetraacetate;NSC 108078
• CAS NO: 43225-70-3
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.276
• Product Categories: Carbohydrate Synthesis;Monosaccharides;Specialty Synthesis
• Mol File: 43225-70-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 140 °C/0.01 mmHg(lit.)
• Flash Point: 168.5°C
• Appearance: /
• Density: 1.31 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.76E-06mmHg at 25°C
• Refractive Index: n20/D 1.4500(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,2,3,5-TETRA-O-ACETYL-ALPHA-D-ARABINOF&(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-TETRA-O-ACETYL-ALPHA-D-ARABINOF&(43225-70-3)
• EPA Substance Registry System: 1,2,3,5-TETRA-O-ACETYL-ALPHA-D-ARABINOF&(43225-70-3)

Safety Data

• Hazard Codes: Xi
• Statements: 43-41
• Safety Statements: 37/39-39-26
• WGK Germany: 3
• Hazardous Substances Data: 43225-70-3(Hazardous Substances Data)

Usage

Uses

It can be used as a reagent in various organic reactions e.g., in the preparation of 5-azacytosine having a cyclic ether substituent at 1-position which can be used as an antitumor agent.

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+,13u/m1/s1

Upstream product

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

Downstream Products

• 461666-78-4 Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester 
• 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 
• 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 
• 1027638-25-0 2-chloro-4-nitrophenyl 2,3,5-tri-O-acetyl-α-L-arabinofuranoside 
• 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 

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 5-deoxy-β-d-galactofuranosides as tools for the characterization of β-d-galactofuranosidases

Derivatives of 5-deoxy-β-d-galactofuranose (5-deoxy-α-l-arabino- hexofuranose) have been synthesized starting from d-galacturonic acid. The synthesis of methyl 5-deoxy-α-l-arabino-hexofuranoside (14α) was achieved by an efficient strategy previously optimized, involving a photoinduced electron transfer (PET) deoxygenation. Compound 14α was converted into per-O-acetyl-5-deoxy-α,β-l-arabino-hexofuranoside (16), an activated precursor for glycosylation reactions. The SnCl4-promoted glycosylation of 16 led to 4-nitrophenyl (19α), and 4-methylthiophenyl 5-deoxy-α-l-arabino-hexofuranosides (20α). The oxygenated analog 4-methylphenyl 1-thio-β-d-galactofuranoside (23β) was also prepared. The 5-deoxy galactofuranosides were evaluated as inhibitors or substrates of the exo-β-d-galactofuranosidase from Penicillium fellutanum, showing that the absence of HO-5 drastically diminishes the affinity for the protein.