trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane

Base Information

• Chemical Name: trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane
• CAS No.: 139757-68-9
• Molecular Formula: C8H11N3O3S
• Molecular Weight: 229.26
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20161162
• Nikkaji Number: J458.017F
• Wikidata: Q83029518
• Mol file: 139757-68-9.mol

Synonyms:139757-68-9;4'-Epi Lamivudine;trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane;4-amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;2(1H)-Pyrimidinone, 4-amino-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-trans)-;4-Amino-1-((2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one;alpha-L-Oxathionyl-cytidine;2(1H)-Pyrimidinone, 4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-trans)-;NCGC00159341-03;3'-Epi lamivudine;.alpha.-L-Oxathionyl-cytidine;SCHEMBL2240686;DTXSID20161162;alpha-L-(+)-(2R,5R)-1-(2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine;5 inverted exclamation mark -Epi Lamivudine;.alpha.-L-(+)-(2R,5R)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine;4-amino-1-[(2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one;rel-4-Amino-1-((2R,5R)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one;(.alpha.-D/.alpha.-L)-(+/-)-(2R,5R)/(2S/5S)-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine

Chemical Property of trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane

Chemical Property:

• Vapor Pressure: 4.91E-11mmHg at 25°C
• Melting Point: 168.0 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 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.: -20°C Freezer
• Solubility.: Methanol (Slightly, Sonicated), 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

4’-EpiLamivudine ^*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: Lamivudine epimer.

Technology Process of trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane

There total 31 articles about trans-2-Hydroxymethyl-5-(cytosin-1-yl)-1,3-oxathiolane 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: 25.0%

(+/-)-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) → 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:

(+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine; With (R)-(-)-N-acetylphenylglycine; In methanol; acetone; at -30 - -20 ℃; for 48h;

With sodium hydroxide; In dichloromethane; water; for 0.5h;

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

Downstream raw materials:

lamivudine

lamivudine

6-[(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-2-(4-nitro-phenyl)-6H-imidazo[1,2-c]pyrimidin-5-one

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.