2',3'-Dideoxy-3'-thiacytidine

Base Information

• Chemical Name: 2',3'-Dideoxy-3'-thiacytidine
• CAS No.: 134680-32-3
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.26
• UNII: H6S9D88T3D
• DSSTox Substance ID: DTXSID301307509
• Nikkaji Number: J409.195G
• Wikidata: Q27279715
• ChEMBL ID: CHEMBL18314
• Mol file: 134680-32-3.mol

Synonyms:2',3' Dideoxy 3' thiacytidine;2',3'-Dideoxy-3'-thiacytidine;2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-;3TC Lamivudine;BCH 189;BCH-189;BCH189;Epivir;GR 109714X;GR-109714X;GR109714X;Lamivudine;Lamivudine, (+)-cis-;Lamivudine, (+-)-trans-;Lamivudine, (2S-cis)-Isomer;Lamivudine, 3TC

Chemical Property of 2',3'-Dideoxy-3'-thiacytidine

Chemical Property:

• Melting Point: 171.4 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 475.4°Cat760mmHg
• PKA: 13.83±0.10(Predicted)
• Flash Point: 241.3°C
• PSA: 116.66000
• Density: 1.73g/cm³
• LogP: -0.25170
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 229.05211239
• Heavy Atom Count: 15
• Complexity: 331

Purity/Quality:

97% ^*data from raw suppliers

ent-Lamivudine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC(S1)CO)N2C=CC(=NC2=O)N
• Isomeric SMILES: C1[C@@H](O[C@@H](S1)CO)N2C=CC(=NC2=O)N
• Uses: An enantiomer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase. ent-Lamivudine (Lamivudine EP Impurity D) is an enantiomer of Lamivudine (L172500); an antiviral that inhibits HIV-reverse transcriptase.

Technology Process of 2',3'-Dideoxy-3'-thiacytidine

There total 22 articles about 2',3'-Dideoxy-3'-thiacytidine 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: 98.0%

cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane (136831-90-8,137125-20-3,137125-21-4,145416-33-7,145985-97-3,145985-98-4,149819-22-7) → (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine (131086-21-0,131086-22-1,134678-17-4,134680-32-3,136846-20-3,136891-12-8,139757-68-9,141434-39-1,146726-78-5)

Guidance literature:

With tetrabutyl ammonium fluoride;

Reference yield: 75.0%

(+)-(2S,5R)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-cystosine (145416-33-7) → lamivudine (131086-21-0,131086-22-1,134678-17-4,136846-20-3,136891-12-8,139757-68-9,141434-39-1,146726-78-5,134680-32-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm00070a006

Reference yield: 72.46%

cis-(+/-)-2-(benzoyloxymethyl)-5-(cytosin-1-yl)-1,3-oxathiolane (S)-mandelate → (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine (131086-21-0,131086-22-1,134678-17-4,134680-32-3,136846-20-3,136891-12-8,139757-68-9,141434-39-1,146726-78-5)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 8 - 10h; Large scale reaction;

DOI:10.1021/op800228h

upstream raw materials:

cis-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-5-(cytosin-1'-yl)-1,3-oxathiolane

cis-2-benzoyloxymethyl-5-(N'4-acetylcytosin-1'-yl)-1,3-oxathiolane

cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane

L-menthyl 5-cytosin-1-yl-1,3-oxathiolane-2-carboxylate

Refernces

• 1、 Ren, Yansong,Hu, Lei,Ramstr?m, Olof. "Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor". . p. 52 - 56. Retrieved 2019/02/24.
• 2、 Hu, Lei,Schaufelberger, Fredrik,Zhang, Yan,Ramstroem, Olof. "Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution". . p. 10376 - 10378. Retrieved 2013/10/22.