[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'-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

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:

C₄₅H₄₈N₅O₁₃PS

3'-O-Acetyl-5'-O-mesyl-thymidin

(R_P)-5'-O-DMT-thymidylyl-(3',5')-3'-O-acetylthymidine 3'-methanephosphonate

(S_P)-5'-O-DMT-thymidylyl-(3',5')-3'-O-acetylthymidine 3'-methanephosphonate

Refernces

• 1、 -. "THERMALLY-CLEAVABLE PROTECTING AND LINKER GROUPS". Page/Page column 8; 70-72. . Retrieved 2018/11/10.
• 2、 Romero, Oscar,Filice, Marco,Guisan, Jose M.,Palomo, Jose M.,De Las Rivas, Blanca,Carrasco-Lopez, Cesar,Hermoso, Juan A.,Klett, Javier,Morreale, Antonio,Abian, Olga. "Semisynthetic peptide-lipase conjugates for improved biotransformations". supporting information. p. 9053 - 9055,3. Retrieved 2020/08/31.