alpha-Thymidine

Base Information

• Chemical Name: alpha-Thymidine
• CAS No.: 4449-43-8
• Molecular Formula: C10H14 N2 O5
• Molecular Weight: 242.232
• Hs Code.: 29349990
• UNII: YMX6U1R2W7
• ChEMBL ID: CHEMBL211174
• DSSTox Substance ID: DTXSID50858957
• Metabolomics Workbench ID: 126890
• Nikkaji Number: J119.617K
• Wikidata: Q81977860
• Mol file: 4449-43-8.mol

Synonyms:alpha-Thymidine;4449-43-8;a-Thymidine;1-(2-Deoxy-alpha-D-ribofuranosyl)-5-methyluracil;YMX6U1R2W7;1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione;L-Thymidine;1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;alpha-D-Thymidine;2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-.alpha.-D-erythro-pentofuranosyl)-5-methyl-;Thymidine alpha-anomer;.ALPHA.-THYMIDINE;UNII-YMX6U1R2W7;NCIMech_000316;.ALPHA.-D-THYMIDINE;SCHEMBL542736;CHEMBL211174;THYMIDINE .ALPHA.-ANOMER;DTXSID50858957;CCG-35534;MFCD00069766;STAVUDINE IMPURITY B [WHO-IP];2'-DEOXY-.ALPHA.-D-RIBOFURANOSYLTHYMINE;EN300-7390661;A826603;BRD-K78278744-001-01-3;1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-oxolanyl]-5-methylpyrimidine-2,4-dione;1-[(2S,4S,5R)-5-(hydroxymethyl)-4-oxidanyl-oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione;1-((2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-(2-DEOXY-.ALPHA.-D-ERYTHRO-PENTOFURANOSYL)-5-METHYLPYRIMIDINE-2,4(1H,3H)-DIONE [WHO-IP];1-[(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-methyl-pyrimidine-2,4-dione

Chemical Property of alpha-Thymidine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 104.55000
• Density: 1.452g/cm³
• LogP: -1.51430
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 242.09027155
• Heavy Atom Count: 17
• Complexity: 381

Purity/Quality:

98%Min ^*data from raw suppliers

a-Thymidine ^*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)O
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@@H]2C[C@@H]([C@H](O2)CO)O
• Uses: α-Thymidine (α-Thymidine) is the unnatural epimer of thymidine. α-Thymidine is an epimer of Thymidine (T412000) and can be used in the synthesis of oligonucleotides containing α-Thymidine.

Technology Process of alpha-Thymidine

There total 54 articles about alpha-Thymidine 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: 95.0%

1-(2-deoxy-3,5-di-p-toluoyl-β-L-ribose)-5-methyluracil (3056-13-1) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With methanol; sodium methylate; at 45 - 50 ℃;

Reference yield: 93.4%

3',5'-di-O-acetyl-β-L-thymidine (433733-94-9) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With ammonia; In methanol; at 6 ℃; for 72h;

Reference yield: 90.0%

3',5'-di-O-levulinoyl-β-L-thymidine (793716-98-0) → C10H14N2O5 (50-89-5,3424-98-4,4449-43-8,4781-17-3,16053-52-4,36646-86-3,39131-66-3,68224-82-8,128112-70-9,131682-41-2,137121-87-0,28854-96-8,3545-96-8,50-88-4) + 3'-O-levulinoyl-β-L-thymidine

Guidance literature:

With Candida antarctica lipase B; phosphate buffer; In 1,4-dioxane; at 30 ℃; for 28.5h; pH=7;

DOI:10.1021/ol048502v

upstream raw materials:

1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)thymine

(5R,6R)-trans-(+)-5-bromo-6-hydroxy-5,6-dihydrothymidine

4-Methyl-benzoic acid (2R,3S,5S)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

3',5'-di-O-p-toluoyl-α-2'-deoxythymidine

Downstream raw materials:

1-[2-deoxy-5-O-(4-methoxytrityl)-α-D-erythro-pentofuranosyl]thymine

C₁₆H₁₈N₄O₈S

C₂₄H₂₅ClN₄O₆

C₂₄H₂₅ClN₄O₆

Refernces

• 1、 Chen, Mengshen,Sinha, Kaustubh,Rule, Gordon S.,Ly, Danith H.. "Interaction of α-Thymidine Inhibitors with Thymidylate Kinase from Plasmodium falciparum". . p. 2868 - 2875. Retrieved 2018/05/14.
• 2、 -. "Method for preparing high-purity telbivudine compound". Paragraph 0046; 0047. . Retrieved 2017/01/02.