131086-21-0Relevant articles and documents
Synthesis of (±)-cis-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine and its (±)-trans isomer
Huang,Rideout,Martin
, p. 195 - 207 (1995)
The title compounds were synthesized by the formation of 2-[(benzyloxy)methyl]-1,3-oxathiolan-5-one and subsequent DIBALH reduction, acetylation, coupling with N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-2-ethylhexanamide and deprotection.
Enzymic Resolution of Oxathiolane Intermediates - An Alternative Approach to the Anti-viral Agent Lamivudine (3TCTM)
Cousins, Rick P.C.,Mahmoudian, Mahmoud,Youds, Peter M.
, p. 393 - 396 (1995)
A number of commercially available lipases and proteases was screened for the ability to hydrolyse enantioselectively racemic oxathiolane 2.Mucor miehei lipase was identified as the most efficient biocatalyst.Bioconversion of 2 afforded enantiomerrically-
Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation
Mear, Sarah Jane,Nguyen, Long V.,Rochford, Ashley J.,Jamison, Timothy F.
, p. 2887 - 2897 (2022/02/07)
By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)
Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor
Ren, Yansong,Hu, Lei,Ramstr?m, Olof
, p. 52 - 56 (2019/02/24)
An enantiopure (2R,5R)-1,3-oxathiolane was obtained using a multienzymatic cascade protocol. By employing a combination of surfactant-treated subtilisin Carlsberg and Candida antarctica lipase B, the absolute configuration of the resulting 1,3-oxathiolane ring was efficiently controlled, resulting in an excellent enantiomeric excess (>99%). This enantiopure 1,3-oxathiolane derivative is a key precursor to anti-HIV agents, such as lamivudine, through subsequent N-glycosylation.
METHODS FOR THE TREATMENT OF HEPATITIS B AND HEPATITIS D VIRUS INFECTIONS
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, (2016/02/26)
It is disclosed a method for treating hepatitis B virus infection or hepatitis B virus/hepatits delta virus co-infection, the method comprising administering to a subject in need of such treatment a first pharmaceutically acceptable agent that comprises at least one phosphorothioated nucleic acid polymer and a second pharmaceutically acceptable agent that comprises at least one nucleoside/nucleotide analog HBV polymerase inhibitor.
Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution
Hu, Lei,Schaufelberger, Fredrik,Zhang, Yan,Ramstroem, Olof
, p. 10376 - 10378 (2013/10/22)
The anti-HIV nucleoside lamivudine was asymmetrically synthesized in only three steps via a novel surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. The enantiomer of lamivudine could also be accessed using the same protocol catalyzed by Candida antarctica lipase B.
OPTICAL RESOLUTION OF SUBSTITUTED 1, 3-OXATHIOLANE NUCLEOSIDES
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, (2011/10/13)
Cis(±)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone is reacted with S(+)-1,1′-binaphthyl-2,2′-diyl hydrogen phosphate in methanol to obtain diastereomeric compounds. The diastereomeric compounds are subjected to selective crystallization to obtain (2R-Cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate. (2R-Cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone 1,1′-binaphthyl-2,2′-diyl hydrogen phosphate is treated with hydrochloric acid in water to obtain (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone.
AN IMPROVED PROCESS FOR THE MANUFACTURE OF LAMIVUDINE
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Page/Page column 14; 18-19, (2011/12/02)
The present invention relates to an improved process for the Manufacture of Lamivudine. A process for the preparation of essentially enantiomerically pure (-)-[2R, 5S]-4-amino-1-[2- (hydroxymethyl)-1,3-oxathiolan-5-y1]-2(1H)-pyrimidin-2-one of formula (I), from L-menthyl glyoxylate is described. Also provided is a process for preparation of (+)-1- (2R/S-Cis)-4-amino-1-[(2-hydroxymethyl)-1,3-oxathiolan-5-y1]-2(1H)-pyrimidin-2-one of formula (XII), from L-menthyl glyoxylate.
OPTICAL RESOLUTION OF SUBSTITUTED 1.3-OXATHIOLANE NUCLEOSIDES
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Page/Page column 13-14, (2010/07/02)
Cis(±)- 4-Amino-1 -[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1 H)- pyrimidinone is reacted with S(+)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate in methanol to obtain diastereomeric compounds. The diastereomeric compounds are subjected to selective crystallization to obtain (2R-Cis)-4-Amino-1-[2- (hydroxymethyl)-i,3-oxathiolan-5-yl]-2(1 H)-pyrimidinone 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate. (2R-Cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5- yl]-2(1 H)-pyrimidinone 1,1 '-binaphthyl-2,2'-diyl hydrogen phosphate is treated with hydrochloric acid in water to obtain (2R-cis)-4-Amino-1-[2-(hydroxymethyl)- 1,3-oxathiolan-5-yl]-2(1 H)-pyrimidinone.
A novel method for large-scale synthesis of lamivudine through cocrystal formation of racemic lamivudine with (S)-(-)-1,1′-Bi(2-naphthol) [(S)-(BINOL)]
Roy, Bhairab Nath,Singh, Girij Pal,Srivastava, Dhananjai,Jadhav, Harishchandra S.,Saini, Manmeet B.,Aher, Umesh P.
experimental part, p. 450 - 455 (2010/04/22)
A large-scale synthesis of (-)-[2R,5S]-4-amino-1- [2-(hydroxymethyl)- 1,3-oxathiolan-5-yl]-2(1H)-pyrimidin-2-one (lamivudine) through resolution of racemic lamivudine by cocrystal formation with (S)- BINOL has been demonstrated. Lamivudine of very high pu
