1,2,3,5-Tetraacetyl-beta-D-ribofuranose (HCID 83064)

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 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|
CAS DataBase Reference: 13035 · 13035-61-5(CAS DataBase Reference)
UNSPSC Code: 12352201 · 12352201
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 280 · P280-P261
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
HS Code: 29400090 · 29400090
Storage Class: 11 · 11 - Combustible Solids
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

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

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.