143919-90-8

Basic information

• Product Name: 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane
• CAS NO: 143919-90-8
• Molecular Weight: 282.317
• Mol File: 143919-90-8.mol

Chemical Properties

• CAS DataBase Reference: 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane(143919-90-8)
• EPA Substance Registry System: 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane(143919-90-8)

Safety Data

• Hazardous Substances Data: 143919-90-8(Hazardous Substances Data)

Upstream product

• 40018-26-6 1,4-dithiane-2,5-diol 
• 64904-47-8 2-benzoyloxyacetaldehyde 
• 122-79-2 Phenyl acetate 
• 108-24-7 acetic anhydride 
• 360778-30-9 trans 2-benzoyloxymethyl-5-hydroxy-1,3-oxathiolane 
• 532-32-1 sodium benzoate 
• 101268-52-4 (benzoyloxy)acetaldehyde diethyl acetal 
• 98-88-4 benzoyl chloride 
• 138760-37-9 2-Benzoyloxymethyl-1,3-oxathiolan-5-one 
• 3376-59-8 2,3-dihydroxypropyl benzoate 
• 98760-27-1 4-benzoyloxymethyl-2,2-dimethyl-[1,3]dioxolane 
• 75-36-5 acetyl chloride 
• 143919-90-8 2-benzoyloxymethyl-5-acethoxy-1,3-oxathiolane 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 1091585-30-6 ((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate 
• 1091585-30-6 TRANS 2-BENZOYLOXYMETHYL-5-(N₄'-ACETYL CYTOSIN-1'-YL)-1,3-OXATHIOLANE 
• 358348-70-6 cis/trans-2-benzoyloxymethyl-5-(cytosin-1'-yl)-1,3-oxathiolane 
• 143919-90-8 ((2R)-5-acetoxy-1,3-oxathiolan-2-yl)methyl benzoate 
• 131086-21-0 lamivudine 
• 134678-17-4 lamivudine 

Relevant articles and documents

Preparation method for emtricitabine isomer

The invention discloses a preparation method for an embritabine isomer. The preparation method comprises the following steps: with Solketal as a starting material, allowing the Solketal to undergo a six-step reaction of esterification, hydrolysis, oxidation, condensation cyclization, acetylation and glycosylation condensation so as to synthesize four mixture intermediates of emtricitabine; and splitting the four isomer intermediates into a cis-isomer mixture and a trans-isomer mixture through a chiral reagent. According to the invention, by adoption of a simple starting material, a mixture forsplitting key intermediates of four optical isomers of the emtricitabine is synthesized through the six-step reaction, and chiral acid is utilized to split the four isomers into a mixture of cis andtrans isomers, so the preparation method provided by the invention has the advantages of simple and convenient operation, high yield and high isomer chiral purity.

Multienzymatic cascade synthesis of an enantiopure (2R,5R)-1,3-oxathiolane anti-HIV agent precursor

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.

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

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.

PROCESS FOR THE MANUFACTURE OF CIS(-)-LAMIVUDINE

An improved process for the manufacture of Lamivudine. The process involves: (a) resolution of racemic lamivudine (intermediate of formula IX) to cis (±) lamivudine of formula (XII) by forming a crystalline salt and separating the product from an organic solvent by fractional crystallization; (b) resolution of cis (±) lamivudine to cis (?) isomer involving formation of S-Binol adduct of formula XIV.

Facile preparation of α-acyloxyacetaldehyde, a versatile intermediate in the synthesis of antiviral nucleosides

This report describes a novel and simple method for the preparation of a versatile intermediate, α-acyloxyacetaldehyde and its acetals, and its application to the synthesis of 4-acetoxy-2-acyloxymethyl-1,3-oxathiolane, an important intermediate in the syn

Preparation of intermediates useful in the synthesis of antiviral nucleosides

The present invention is an efficient process for the manufacture of α-acyloxyacetaldehyde, a key intermediate in the synthesis of 1,3-oxathiolane and 1,3-dioxolane nucleosides.

PROCESS FOR PREPARING SUBSTITUTED 1,3-OXATHIOLANES WITH ANTIVIRAL PROPERTIES

Disclosed are processes for preparing compounds of formula (I) and pharmaceutically acceptable salts or esters thereof, wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S = O or SO2. The invention also relates to

Processes for preparing substituted 1,3-oxathiolanes with antiviral properties

Disclosed are processes for preparing compounds of the formula (I) and pharmaceutically acceptable salts or esters thereof: STR1 wherein R2 is a purine or pyrimidine base or an analogue or derivative thereof; and Z is S, S=O or SO2.