[2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] acetate

Base Information

• Chemical Name: [2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] acetate
• CAS No.: 21090-30-2
• Molecular Formula: C12H16N2O6
• Molecular Weight: 284.269
• NSC Number: 130219
• DSSTox Substance ID: DTXSID40943402
• Mol file: 21090-30-2.mol

Synonyms:21090-30-2;3'-O-Acetylthymidine;[2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] acetate;[2-(hydroxymethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] acetate;NSC130219;DTXSID40943402;IRFKBRPHBYCMQU-UHFFFAOYSA-N;AKOS003382385;NSC-130219;FT-0638092;A815133;[2-(hydroxymethyl)-5-[5-methyl-2,4-bis(oxidanylidene)pyrimidin-1-yl]oxolan-3-yl] ethanoate;1-(3-O-Acetyl-2-deoxypentofuranosyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one;acetic acid [2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-1-pyrimidinyl)-3-oxolanyl] ester;2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate

Chemical Property of [2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] acetate

Chemical Property:

• Melting Point: 174 °C
• Boiling Point: °Cat760mmHg
• PKA: 9.55±0.10(Predicted)
• Flash Point: °C
• PSA: 110.62000
• Density: 1.42g/cm³
• LogP: -0.94350
• Storage Temp.: Store at 0-5°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 284.10083623
• Heavy Atom Count: 20
• Complexity: 475

Purity/Quality:

98%, ^*data from raw suppliers

3''-O-Acetylthymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)OC(=O)C
• General Description: 3'-Acetylthymidine (also known as 3'-O-acetylthymidine or thymidine 3'-acetate) is a chemically modified nucleoside derivative used as an intermediate or reactant in oligonucleotide synthesis, particularly in the preparation of dinucleoside phosphorodithioates, phosphorothioates, and methanephosphonates. It serves as a protected thymidine unit, enabling controlled elongation of oligonucleotide chains while maintaining stereochemical integrity. 3'-ACETYLTHYMIDINE is employed in synthetic strategies for producing nuclease-resistant oligonucleotide analogues with potential therapeutic applications, such as antisense and antigene therapies. Its 3'-O-acetyl group provides transient protection during coupling reactions, facilitating the formation of diastereomerically pure oligomeric structures.

Technology Process of [2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] acetate

There total 13 articles about [2-(Hydroxymethyl)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)oxolan-3-yl] 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: 91.0%

3',5'-diacetylthymidine (6979-97-1,97834-40-7,142405-86-5) → 3'-O-acetylthymidine (21090-30-2) + 5'-O-acetylthymidine (35898-31-8) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With sodium acetate; In acetonitrile; at 25 ℃; for 72h; pH=5; regioselective reaction;

DOI:10.1039/c2cc34816k

Reference yield: 74.0%

3'-O-acetyl-5'-O-triphenylmethylthymidine (23583-46-2) + benzyl alcohol (100-51-6,185532-71-2) → triphenylmethane (519-73-3) + benzyl trityl ether (5333-62-0) + 3'-O-acetylthymidine (21090-30-2) + thymin (65-71-4,28806-14-6,691841-57-3)

Guidance literature:

With copper(II) sulfate; In xylene; for 2h; Heating;

DOI:10.1080/15257770802257846

Reference yield: 69.0%

(2R,3S,5R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate (56070-42-9) + benzyl alcohol (100-51-6,185532-71-2) → (benzyloxy)(tert-butyl)dimethylsilane (53172-91-1) + 3'-O-acetylthymidine (21090-30-2) + thymin (65-71-4,28806-14-6,691841-57-3) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With copper(II) sulfate; In xylene; for 2h; Heating;

DOI:10.1080/15257770802257846

upstream raw materials:

acetic anhydride

thymidine

Acetic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[2-(pyridin-2-ylamino)-ethoxycarbonyloxymethyl]-tetrahydro-furan-3-yl ester

(2R,3S,5R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl acetate

Downstream raw materials:

3'-O-toluoyl-β-thymidine

thymidine 5'-phosphate

<(MeO)2Tr>C^bzpTOAc

<(MeO)2Tr>A^bzpTOAc

Refernces

NUCLEOSIDE PHOSPHONODITHIOATES AS INTERMEDIATES IN THE PREPARATION OF DINUCLEOSIDE PHOSPHORODITHIOATES AND PHOSPHOROTHIOATES

10.1016/S0040-4039(01)80782-6

The research focuses on the synthesis of dinucleoside phosphorodithioates and phosphorothioates, which are analogues of oligonucleotides with potential applications as antiviral agents and in studies involving interactions with nucleic acids and proteins. The purpose of the study is to develop an alternative and convenient approach to synthesizing these analogues using protected nucleoside 3'-phosphonodithioates as starting materials. The researchers successfully converted 5'-O-(9-phenylxanthen-9-yl)thymidine into its 3'-phosphonodithioate derivative and further into dinucleoside phosphonothioate and dinucleoside phosphorodithioate with good overall yields. Key chemicals used in the process include triethylammonium salt, 3'-O-acetylthymidine, pivaloyl chloride, and sulfur. The study concludes that the procedure is potentially applicable to the synthesis of phosphorodithioate analogues of oligodeoxyribo- and oligoribo-nucleotides, both in solution and on solid supports, and that the synthesized dinucleoside phosphorodithioate (6a) is resistant to digestion by snake venom phosphodiesterase, bovine spleen phosphodiesterase, and nuclease PI.

Oligomeric building block approach to the synthesis of diastereomerically pure pentathymidine 3′,5′-methanephosphonates

10.1021/ol991376o

The research presents a method for the large-scale synthesis of stereodefined oligo(nucleoside 3',5'-methanephosphonates) (oligo-PMe), which are potential candidates for drugs in antisense and antigene strategies due to their sequence-specific recognition, nuclease resistance, and ability to access intracellular environments. The study focuses on developing a strategy to synthesize diastereomerically pure oligo-PMe through transient 3'-O protection, allowing the conversion of a chirally defined methanephosphonanilidate group into diastereomerically pure "oligomeric building blocks" for stereospecific coupling. 3'-O-acetylthymidine is used as a reactant in the condensation reaction with compound 2 to form the dinucleoside methanephosphonate (4). It provides the thymidine nucleoside unit necessary for the elongation of the oligonucleotide chain. Trichloroacetic acid is used to selectively remove the 5'-O protective group from the methanephosphonanilidate, yielding the corresponding 5'-OH compound. This step is crucial for the subsequent coupling reactions.