528567-32-0

Basic information

• Product Name: 1,3-Oxathiolane-2-methanol,5-methoxy-,(2R)-(9CI)
• Synonyms: 1,3-Oxathiolane-2-methanol,5-methoxy-,(2R)-(9CI);(2R)-5-Methoxy-1,3-oxathiolane-2-Methanol
• CAS NO: 528567-32-0
• Molecular Formula: C5H10O3S
• Molecular Weight: 150.2
• Product Categories: METHOXY;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 528567-32-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform
• CAS DataBase Reference: 1,3-Oxathiolane-2-methanol,5-methoxy-,(2R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Oxathiolane-2-methanol,5-methoxy-,(2R)-(9CI)(528567-32-0)
• EPA Substance Registry System: 1,3-Oxathiolane-2-methanol,5-methoxy-,(2R)-(9CI)(528567-32-0)

Safety Data

• Hazardous Substances Data: 528567-32-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Intermediate in the preparation of Lamivudine (L172500).

Upstream product

• 1091585-27-1 C₁₆H₂₈O₅S 
• 1091585-26-0 C₁₅H₂₆O₄S 
• 528567-31-9 menthyl 5-hydroxy[1,3]oxathiolane-2-carboxylate 

Relevant articles and documents

Method for synthesizing lamivudine intermediate

The present invention discloses a synthetic method of lamivudine intermediate, the method comprises the following steps: a compound of formula V is obtained by methoxylation reaction of a compound of formula VI and a hydrochloric acid methanol solution; a compound of formula IV is obtained by reduction reaction of the compound of formula V and sodium borohydride in ethanol; a compound of formula III is obtained by esterification reaction of the compound of formula IV and chlorinated carbonate under the effect of an organic base for formation of bicyclic carboxylic ester; a compound of formula II is obtained by acylation reaction of the compound of formula III and acetic anhydride under the acid catalysis; a meso compound of the formula I' is obtained by glycosylation reaction of the compound of formula II and silane protected N4-acetamido cytosine under the Iodotrimethylsilane catalysis; and the lamivudine intermediate as shown in the formula I is obtained by recrystallization resolution of the meso compound of the formula I'. The method has the advantages of being simple in operation, low in cost, high in product purity, and the like.

A PROCESS FOR STEREOSELECTIVE SYNTHESIS OF LAMIVUDINE

The present invention discloses a process for stereoselective synthesis of Lamivudine comprising the following steps: (a) performing a glycosylation reaction between the compound of formula (I) and cytosine or protected cytosine, and separating the reaction product by recrystallization to obtain the intermediate of formula (II); and (b) deprotecting the intermediate of formula (II) to obtain Lamivudine.

Synthesis of oxathiolane imidazole nucleosides

Nucleosides have been of great interest since their strong antiviral activities were discovered. 1,3-Oxathiolane ring system has been known for many years, but it is in recent years that the ring has been used as the sugar ring in nucleoside analogs (Synthesis (1991) 1046; J. Am. Chem. Soc. 113 (1991) 9377; Tetrahedron Lett. 35 (1994) 4739). Besides, bredinin is a natural nucleoside antibiotic with imidazole moiety and there are some other studies reported on nucleosides with the imidazole group (Biorg. Med. Chem. 7 (1999) 481; Biorg. Med. Chem. 7 (1999) 1617; Nucleosides Nucleotides 18 (1999) 331). These findings make the imidazole group interesting as the base of a nucleoside. In this study, in order to find out the structure-activity relationships of L-oxathiolanyl nucleosides, L-oxathiolanyl imidazole nucleosides 7 and 8 were synthesized, via novel intermediates 2-6, which were then tested for anti-HIV activity (Antivir. Res. 1-11 (1994) 25) in human peripheral blood mononuclear (PBM) cells, the synthesized nucleosides did not show significant activity up to 100 μM against HIV-1.