1,2,3,5-Tetraacetyl-beta-D-ribofuranose
Completing data — refresh the page later to see the latest
Basic information
- CAS
13035-61-5- Standard SMILES
CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O- InChIKey
IHNHAHWGVLXCCI-FDYHWXHSSA-N- Molecular formula
- C13H18O9
- Average molar mass
- 318.28 g/mol
- Monoisotopic mass
- 318.09508215
Names & identifiers
- Preferred name
- 1,2,3,5-Tetraacetyl-beta-D-ribofuranose
- IUPAC
- [(2R,3R,4R,5S)-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-Tetraacetyl-beta-D-ribofuranoseEINECS 235-898-5beta-D-Ribofuranose, tetraacetateNSC 18738beta-D-Ribofuranose, 1,2,3,5-tetraacetateRefChem:410632235-898-513035-61-5beta-D-Ribofuranose 1,2,3,5-tetraacetate1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranoseTetra-O-acetyl-beta-D-ribofuranoseMFCD00005358
Show more names
TETRAACETYLRIBOFURANOSEbeta-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
(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate1,2,3,5-Tetraacetyl-.-d-ribofuranoseDTXSID9057632[(2R,3R,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate1,2,3,5-Tetraacetyl-ss-D-ribofuranosebeta-d-ribofuranose-1,2,3,5-tetraacetate.beta.-D-Ribofuranose, tetraacetate
Database identifiers
- CAS
13035-61-5- PubChem CID
- 83064
- DTXSID
DTXSID9057632- ChEMBL
CHEMBL3183254- UNII
- LVQ7CQ9SBR
- EC Number
- 235-898-5
- Nikkaji
- J259C
Properties
Computed structural propertiesFilling in
- XLogP
- 0.7
- Topological polar surface area
- 114 Ų
- 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 information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 72.7% (8 of 11) of all reports.
Warning
H315 (27.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (27.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (27.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 11 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 8 of 11 reports by companies.；There are 3 notifications provided by 3 of 11 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory InformationStatus: Active Update: 18-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26235
Hazard Classes and CategoriesSkin Irrit. 2 (27.3%)；Eye Irrit. 2 (27.3%)；STOT SE 3 (27.3%)
Regulatory information
Regulatory InformationStatus: Active Update: 18-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26235
Chemistry & industry
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
59 records
Compound notes
Loading…