CAS 13035-61-5 1,2,3,5-Tetra-O-acetyl-beta-L-ribofuranose (HCID 227274)

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Basic information

CAS: 13035-61-5
Standard SMILES: CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C1OC(C)=O
InChIKey: IHNHAHWGVLXCCI-UHFFFAOYSA-N
Molecular formula: C13H18O9
Average molar mass: 318.28 g/mol

Names & identifiers

Preferred name: 1,2,3,5-Tetra-O-acetyl-beta-L-ribofuranose
IUPAC: (3,4,5-triacetyloxyoxolan-2-yl)methyl acetate
English name: beta-D-Ribofuranose 1,2,3,5-tetraacetate
Molecular formula: C13H18O9
Molecular weight: 318.28

Names & synonyms

1,2,3,5-Tetra-O-acetylpentofuranose1,2,3,5-Tetra-O-acetyl-beta-L-ribofuranoseTetraacetylribofuranose1,2,3,5-TETRA-O-ACETYL-ALPHA-L-ARABINOF&105453-36-91,2,3,5-TETRA-O-ACETYL-beta-L-XYLOFURANOSE.beta.-D-Ribofuranose, tetraacetateNSC-18738Tetra-O-acetyl-.beta.-D-ribofuranose(3,4,5-triacetyloxyoxolan-2-yl)methyl acetate.beta.-D-Ribofuranose tetraacetate1,2,3,5-tetra-O-acetyl-L-ribofuranose

Show more names

(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetatebeta-D-Ribofuranose1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSETETRA-O-ACETYL-BETA-D-RIBOFURANOSE1,2,3,5-Tetraacetate1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose1,2,3,5-tera-O-acetyl-beta-D-ribofuranoseBETA-D-RIBOFURANOSE 1,2,3,5-TETRA-O-ACETATE[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate

beta-D-Ribofuranose1,2,3,5-tetraacetateRibofuranose, .beta.-D-Oprea1_258250SCHEMBL5410915NSC18738SBA92746BBL029398NSC108078

Properties

Computed structural properties

XLogP: 0.7
Topological polar surface area: 114 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 9
Rotatable bonds: 9
Heavy atoms: 22
Formal charge: 0
Complexity: 458

Physicochemical properties

Melting point: 81 · 81-83 °C(lit.)
alpha: -15.4 · -15.4 º (c=7, MeOH)
Boiling point: 417.45 °C · 417.45°C (rough estimate)
Density: 1.4171 · 1.4171 (rough estimate)
refractive index: -14.5 ° · -14.5 ° (C=5, MeOH)
storage temp.: Inert atmosphere,Room Temperature
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Crystalline Powder
color: White to almost white
optical activity: 26 · [α]26/D 11.4°, c = 10 in chloroform
BRN: 94078 · 94078
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-/s3
InChIKey: TTXVPMATRDJQIA-BKUVIOGVSA-N
SMILES: [C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H]1OC(=O)C |&1:0,5,12,17,r|

Safety & regulation

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29400090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
REACH Registrations: Active
Precautionary statements: P280-P261

Chemistry & industry

Applications · 2 items

Descriptionbeta-D-Ribofuranose 1,2,3,5-tetraacetate is an acetylated derivative of ribose extensively used in carbohydrate research and synthetic chemistry. This compound features acetyl groups protecting the hydroxyl functionalities at positions 1, 2, 3, and 5 of the ribofuranose ring, which enhances its stability and solubility in organic solvents. β-D-Ribofuranose 1,2,3,5-tetraacetate is a crucial intermediate in synthesising nucleosides, nucleotides, and other complex carbohydrates. In research, it is utilized to study glycosylation mechanisms, focusing on the formation and stereochemistry of glycosidic bonds.

Usesbeta-D-Ribofuranose 1,2,3,5-tetraacetate is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine.