(3,5-Diacetyloxyoxolan-2-yl)methyl acetate

Base Information

• Chemical Name: (3,5-Diacetyloxyoxolan-2-yl)methyl acetate
• CAS No.: 4594-52-9
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.244
• NSC Number: 138278
• DSSTox Substance ID: DTXSID60963465
• Mol file: 4594-52-9.mol

Synonyms:1,3,5-tri-o-acetyl-2-deoxypentofuranose;(3,5-diacetyloxyoxolan-2-yl)methyl acetate;a-D-erythro-Pentofuranose, 2-deoxy-, triacetate;NSC138278;D-erythro-Pentofuranose, 2-deoxy-, 1,3,5-triacetate;[(2R,3S,5S)-3,5-diacetyloxyoxolan-2-yl]methyl acetate;SCHEMBL6382722;DTXSID60963465;NSC-138278;FT-0698432;1,3,5-Tri-O-acetyl-2-deoxy-|A-D-erythro-pentofuranose

Chemical Property of (3,5-Diacetyloxyoxolan-2-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 0.000179mmHg at 25°C
• Refractive Index: 1.466
• Boiling Point: 329.297 °C at 760 mmHg
• Flash Point: 142.967 °C
• PSA: 88.13000
• Density: 1.241 g/cm³
• LogP: 0.15930
• Storage Temp.: 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 260.08960285
• Heavy Atom Count: 18
• Complexity: 338

Purity/Quality:

99% ^*data from raw suppliers

1,3,5-Tri-O-acetyl-2-deoxy-D-ribose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)OC(=O)C)OC(=O)C
• Uses: 1,3,5-Tri-O-acetyl-2-deoxy-D-ribose is used in the chemoenzymic preparation of nucleosides.

Technology Process of (3,5-Diacetyloxyoxolan-2-yl)methyl acetate

There total 11 articles about (3,5-Diacetyloxyoxolan-2-yl)methyl acetate 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: 93.0%

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + acetic anhydride (108-24-7) → 1,3,5-tri-O-acetyl-2-deoxyribose (4594-52-9,96291-74-6,96291-75-7)

Guidance literature:

With pyridine; In 1,4-dioxane; for 3h; Reflux;

DOI:10.3390/molecules17044343

Reference yield: 84.0%

acetic anhydride (108-24-7) + 2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-erythropentofuranose → 1,3,5-tri-O-acetyl-2-deoxyribose (4594-52-9,96291-74-6,96291-75-7)

Guidance literature:

With perchloric acid immobilized on silica gel; In dichloromethane; for 4h; Reflux;

DOI:10.1016/j.tet.2010.12.028

Reference yield: 63.3%

acetic anhydride (108-24-7) + 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside (151767-35-0) → 1,3,5-tri-O-acetyl-2-deoxyribose (4594-52-9,96291-74-6,96291-75-7)

Guidance literature:

With sulfuric acid; acetic acid; at 6 - 20 ℃; for 5.66h; Inert atmosphere; Industry scale;

upstream raw materials:

2-Deoxy-D-ribose

acetic anhydride

2-deoxy-D-ribose

D-2-deoxyribose

Downstream raw materials:

Acetic acid (2R,3S)-2-acetoxymethyl-5-(3-benzyloxy-2-methyl-4-oxo-4H-pyridin-1-yl)-tetrahydro-furan-3-yl ester

3',5'-diacetylthymidine

stavudin

3',4'-anhydrothymidine

Refernces

• 1、 -. "SYNTHESIS AND IMPROVEMENT OF A NUCLEOSIDE ANALOGUE AS AN ANTI-CANCER AND ANTI-VIRAL DRUG". Page/Page column 6-7; 13. . Retrieved 2021/05/29.
• 2、 Psykarakis, Emmanuel E.,Chatzopoulou, Elli,Gimisis, Thanasis. "First characterisation of two important postulated intermediates in the formation of a HydT DNA lesion, a thymidine oxidation product". . p. 2289 - 2300. Retrieved 2018/04/05.