beta-D-Ribofuranose 1,2,3,5-tetraacetate

Base Information

• Chemical Name: beta-D-Ribofuranose 1,2,3,5-tetraacetate
• CAS No.: 13035-61-5
• Deprecated CAS: 82264-12-8
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• Hs Code.: 29400090
• European Community (EC) Number: 235-898-5
• DSSTox Substance ID: DTXSID9057632
• Nikkaji Number: J259C
• Wikidata: Q72506691
• ChEMBL ID: CHEMBL3183254
• Mol file: 13035-61-5.mol

Synonyms:13035-61-5;beta-D-Ribofuranose 1,2,3,5-tetraacetate;Tetra-O-acetyl-beta-D-ribofuranose;1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranose;MFCD00005358;(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate;1,2,3,5-Tetraacetyl-.-d-ribofuranose;1,2,3,5-tetra-o-acetyl-b-d-ribofuranose;.beta.-D-Ribofuranose, tetraacetate;EINECS 235-898-5;[(2R,3R,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate;Ribofuranose, tetraacetate, .beta.-D-;1,2,3,5-Tetraacetyl-beta-D-ribofuranose;tetra-o-acetyl-b-d-ribofuranose;DTXSID9057632;1,2,3,5-Tetra-O-acetyl beta-D-Ribofuranose;Tetra-O-acetyl-.beta.-D-ribofuranose;Tetraacetylribofuranose;1,2,3,5-Tetra-O-acetylpentofuranose #;(2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]tetrahydro-3-furanyl acetate;tetraacetylribose;C13-H18-O9;1,2,3,5-Tetraacetyl-|A-D-ribose;SCHEMBL77518;CHEMBL3183254;DTXCID0031421;Tetraacetyl-beta-D-ribofuranoside;beta-D-Ribofuranose, tetraacetate;Tox21_113750;[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate;NSC 18738;AKOS015920139;AKOS015995010;AC-8170;AM83967;CS-W019120;1,2,3,5-Tetraacetyl-ss-D-ribofuranose;NCGC00253620-01;AK-50517;DS-15484;1,2,3,5-Tetraacetyl-.beta.-ribofuranose;beta-d-ribofuranose-1,2,3,5-tetraacetate;CAS-13035-61-5;beta -D-Ribofuranose 1,2,3,5-tetraacetate;R0066;.beta.-D-Ribofuranose 1,2,3,5-tetraacetate;1,2,3,5-tetra-O-acetyl-beta -D-ribofuranose;1,2,3,5-tetra-O-Acetyl-.beta.-D-ribofuranose;A806070;beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98%;SR-01000944731;SR-01000944731-1

Chemical Property of beta-D-Ribofuranose 1,2,3,5-tetraacetate

Chemical Property:

• Appearance/Colour: white to almost white crystalline powder
• Vapor Pressure: 3.76E-06mmHg at 25°C
• Melting Point: 81-83 °C(lit.)
• Refractive Index: -14.5 ° (C=5, MeOH)
• Boiling Point: 385.6 °C at 760 mmHg
• Flash Point: 168.5 °C
• PSA: 114.43000
• Density: 1.29 g/cm³
• LogP: -0.29910
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 318.09508215
• Heavy Atom Count: 22
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

1,2,3,5-Tetra-O-acetyl β-D-Ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: beta-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. 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.

Technology Process of beta-D-Ribofuranose 1,2,3,5-tetraacetate

There total 84 articles about beta-D-Ribofuranose 1,2,3,5-tetraacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

acetic anhydride (108-24-7) + methyl 2,3,5-tri-O-acetyl-α,β-D-arabinofuranoside (90244-44-3,110415-62-8) → 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9,43225-70-3)

Guidance literature:

With sulfuric acid; In acetic acid;

DOI:10.3987/COM-08-S(F)59

Reference yield: 86.0%

acetic anhydride (108-24-7) + G (118-00-3) → 2,9-diacetylguanine (3056-33-5) + 1,2,3,5-tetraacetylribose (13035-61-5)

Guidance literature:

acetic anhydride; G; at 136 ℃; for 1h;

With trifluoroacetic acid; at 60 - 100 ℃;

DOI:10.1080/00304948.2012.697741

Reference yield:

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → 1,2,3,6-tetra-O-acetyl-5-deoxy-α-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,6-tetra-O-acetyl-5-deoxy-β-L-arabino-hexofuranose (13035-61-5,23094-61-3,28708-32-9,39727-26-9,42927-46-8,43225-70-3,50730-26-2,56272-01-6,61248-15-5,61826-42-4,61849-90-9,69855-18-1,69855-19-2,79120-80-2,79120-81-3,86782-36-7,86782-94-7,105453-36-9,144490-03-9) + 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) + 1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

With pyridine; at 0 ℃; Yield given. Yields of byproduct given;

upstream raw materials:

5-O-triphenylmethyl-D-ribofuranose-1,2,3-triacetate

Acetyl bromide

acetic anhydride

pyridine

Downstream raw materials:

2',3',5'-tri-O-acetyl-5-[(benzyloxy)methyl]uridine

1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-cyano-6-phenyl-2-thiouracil

Acetic acid (2S,3R,4S,5S)-4-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenoxy)-tetrahydro-furan-3-yl ester

2',3',5'-triacetyl ethyl nicotinate riboside

Refernces

• 1、 Viscontini et al.. "-". . p. 1373,1375. Retrieved 1954.
• 2、 Gao, Mingzhang,Chen, Yiwen,Tan, Songde,Reibenspies, Joseph H.,Zingaro, Ralph A.. "Syntheses of 1-thio-D-xylose and D-ribose esters of diorganoarsinous acids and their anticancer activity". . p. 199 - 206. Retrieved 2008.
• 3、 Chittenden. "-". . p. 491. Retrieved 1972.
• 4、 Andreeva,Saifina,Belenok,Semenov,Kataev. "The First Analog of Pyrimidine Nucleosides with Two Nucleobases and Two d-Ribofuranose Residues". . p. 292 - 296. Retrieved 2021/03/26.
• 5、 Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun. "A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction". supporting information. . Retrieved 2020/03/30.