1,3,5-Tri-O-benzoyl-a-D-ribofuranose

Name: 1,3,5-Tri-O-benzoyl-a-D-ribofuranose
SKU: ACM171866301
Rating: 5 (1 reviews)

CAS

171866-30-1

Catalog Number

ACM171866301

Category

Main Products

Molecular Weight

462.40

Molecular Formula

C26H22O8

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Specification

Synonyms

(2S,3S,4R,5S)-5-((BENZOYLOXY)METHYL)-3-HYDROXYTETRAHYDROFURAN-2,4-DIYL DIBENZOATE

Appearance

White to off-white powder or crystals

1,3,5-Tri-O-Benzoyl-α-D-Ribofuranose for the Stereoselective Synthesis of N-Glycosyl Oxazolines

Sivets, Grigorii G., et al. Journal of New Devel-opments in Chemistry, 2023, 4 (2), 1-23.

The research demonstrated a stereoselective synthesis technique for protected N-glycosyl oxazolines starting from accessible acylated sugar 1,2-O-acetone compounds through an intramolecular Ritter-type reaction. The synthesis process involved production of 2-methyl-(3,5-di-O-benzoyl-α-D-ribofuranose)-[1,2-d]-2-oxazoline (13) using 1,3,5-tri-O-benzoyl-α-D-ribofuranose (50) as the reaction raw material.
Synthetic procedure
· Route b2: The stirred mixture of 1,3,5-tri-O-benzoyl-α-D-ribofuranose 50 (250 mg, 0.54 mmol) dissolved in anhydrous acetonitrile (10.0 ml) underwent sequential treatment with KHF2 (156 mg, 1.99 mmol) and boron trifluoride diethyl etherate (0.39 ml, 3.08 mmol). After maintaining the reaction at room temperature for 3.5 hours, transferred it to cooled 1N aqueous NaOH. The work-up process led to the production of oxazoline 13 which appeared as a colorless oil and weighed 204 mg with a 99% yield.
· Route c2. A ribofuranose derivative solution 50 (100 mg, 0.22 mmol) was prepared in anhydrous acetonitrile (4.0 ml) before the addition of boron trifluoride diethyl etherate (0.16 ml, 1.26 mmol). The reaction proceeded with stirring at room temperature for 3.5 hours before the contents were decanted into 2.7 ml of cooled 1N aqueous NaOH. Following work-up procedures oxazoline 13 (90 mg) was obtained as a yellowish oil which had a yield of 65% according to 1H NMR measurements in CDCl3.

1,3,5-tri-O-benzoyl-α-L-ribofuranose for the Total Synthesis of 2'-O-methyl-β-l-arabinosyluridine

Shen, Chunyang, et al. Phytochemistry Letters, 2020, 36, 68-72.

· The synthesis of 2'-O-methyl-L-arabinosyluridine began with 1,3,5-tri-O-benzoyl-α-L-ribofuranose 4 preparation from L-ribose in four steps that produced a 52% overall yield as documented in literature.
· 2-O-Trifluoromethylsulfonyl-1,3,5-tri-O-benzoyl-α-L-ribofuranose 5 achieved a 90 % yield through esterification with trifluoromethanesulfonic anhydride in anhydrous pyridine and DCM mixture. The triflate 5 underwent nucleophilic substitution using KNO2 and simultaneous hydrolysis in water to produce 1,3,5-tri-O-benzoyl-α-L-arabinofuranose 6 with 52 % yield.
· Then turned the attention to the methylation process of the 2-OH group in compound 6. The optimal reaction conditions emerged after thorough optimization of solvents and reaction temperature with specific equivalence ratios of TMSCHN2 and HBF4 which established 1.0 equiv as the best parameter. 1,3,5-tri-O-benzoyl-α-L-arabinofuranose 6, 2.0 equiv. of TMSCHN2, and 1.0 equiv. of HBF4 in DCM at room temperature. The reaction produced methyl ether 7 at a 70 % yield while leaving 20 % of the starting material arabinose 6 unreacted.
· Methyl ether 7 underwent Vorbrüggen glycosylation with uracil using MeCN/BSA/TMSOTf as reaction conditions. It afforded the β-L-arabinosyluridine 8 and α-L-arabinosyluridine 9 (approximation ratio of 3:1) as expected in 74 % yield. The mixed isomers yield some nucleoside 8 as a white solid when recrystallized with precision. Nucleosides 1 and 2 were obtained by treating the mixture with a saturated solution of ammonia in methanol then separating these products through HPLC.

What is the molecular formula of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The molecular formula is C26H22O8.

What are the synonyms for 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The synonyms are 22224-41-5, 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose, and [(2R,3S,4R,5R)-3,5-dibenzoyloxy-4-hydroxyoxolan-2-yl]methyl benzoate.

What is the molecular weight of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The molecular weight is 462.4 g/mol.

What is the IUPAC name of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The IUPAC name is [(2R,3S,4R,5R)-3,5-dibenzoyloxy-4-hydroxyoxolan-2-yl]methyl benzoate.

What is the InChI of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The InChI is InChI=1S/C26H22O8/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26-27H,16H2/t20-,21-,22-,26-/m1/s1.

What is the InChIKey of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The InChIKey is HUHVPBKTTFVAQF-PIXQIBFHSA-N.

What is the canonical SMILES of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The canonical SMILES is C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)OC(=O)C3=CC=CC=C3)O)OC(=O)C4=CC=CC=C4.

How many hydrogen bond donor count does 1,3,5-Tri-O-benzoyl-a-D-ribofuranose have?

It has 1 hydrogen bond donor count.

How many hydrogen bond acceptor count does 1,3,5-Tri-O-benzoyl-a-D-ribofuranose have?

It has 8 hydrogen bond acceptor count.

What is the topological polar surface area of 1,3,5-Tri-O-benzoyl-a-D-ribofuranose?

The topological polar surface area is 108Å².