817204-32-3

Basic information

• Product Name: PSI-6130 derivative
• Synonyms: Cytidine, N-benzoyl-2'-deoxy-2'-fluoro-2'-Methyl-, 3',5'-dibenzoate, (2'R)-;PSI-6130 derivative;2'-Deoxy-2'-fluoro-2'- Methyl-N-(phenylcarbonyl) cytidine;(2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-Methylcytidine 3',5'-dibenzoate;3',5'-O-4-Tribenzoyl-2'-deoxy-2'-fluoro-2'-C-Methylcytidine;(2R,3R,4R,5R)-5-(4-benzaMido-2-oxopyriMidin-1(2H)-yl)-2-((benzoyloxy)Methyl)-4-fluoro-4-Methyltetrahydrofuran-3-yl benzoate;(2R,3R,4R,5R)-5-(4-benzaMido-2-oxopyriMidin-1(2H)-yl);InterMediate of Sofosbuir
• CAS NO: 817204-32-3
• Molecular Formula: C₃₁H₂₆FN₃O₇
• Molecular Weight: 571.5524432
• EINECS: 1308068-626-2
• Product Categories: Sofosbuvir intermediate
• Mol File: 817204-32-3.mol

Chemical Properties

• Melting Point: 241℃ (dichloromethane hexane )
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 8.51±0.20(Predicted)
• CAS DataBase Reference: PSI-6130 derivative(CAS DataBase Reference)
• NIST Chemistry Reference: PSI-6130 derivative(817204-32-3)
• EPA Substance Registry System: PSI-6130 derivative(817204-32-3)

Safety Data

• Hazardous Substances Data: 817204-32-3(Hazardous Substances Data)

Usage

Uses

2’-Defluro-2’-methylene Sofosbuvir is an impurity of Sofosbuvir (P839640).

Upstream product

• 1500076-79-8 (2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate 
• 85743-99-3 N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide 
• 874638-93-4 (2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate 
• 874638-80-9 ((2R,3R,4R)-3-benzoyloxy-4-fluoro-4-methyl-5-oxo-tetrahydrofuran-2-yl)methyl benzoate 
• 26661-13-2 N₄-benzoylcitosine 
• 914912-73-5 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose 
• 863329-62-8 N⁴-benzoyl-1-(2-C-methyl-3,5-di-O-benzoyl-β-D-arabinofuranosyl)cytosine 
• 26661-13-2 4-N-benzoylcytosine 
• 64339-87-3 N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine 
• 98-88-4 benzoyl chloride 
• 30361-18-3 3.5-Di-O-benzoyl-2-C-methyl-α-D-ribofuranose 
• 729596-46-7 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone 
• 1199809-23-8 ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate 
• 1199809-22-7 ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl benzoate 

Downstream Products

• 1064684-44-1 sofosbuvir 
• 1190307-88-0 sofosbuvir 
• 1064684-24-7 (S)-2-{(4-bromophenoxy)-[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}-3-methylbutyric acid methyl ester 
• 1064684-25-8 (S)-2-{(4-bromophenoxy)[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy]phosphorylamino}propionic acid methyl ester 
• 1064684-23-6 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}-3-methylbutyric acid methyl ester 
• 1015255-46-5 (S)-2-{[(2R,3R,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyltetrahydrofuran-2-ylmethoxy](phenoxy)phosphorylamino}propionic acid methyl ester 
• 874638-98-9 N-(1-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 
• 863329-66-2 2'-deoxy-2'-fluoro-2'-methyluridine 
• 863329-65-1 (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate 
• 817204-33-4 (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine 

Relevant articles and documents

Preparation method of intermediate

The invention relates to the technical field of biological pharmacy. More specifically, the compound shown in Formula -3 - is prepared by reacting a compound represented by Formula -4 - with a modified 4R red aluminum, and then subjecting the compound of

Method for preparing sofosbuvir intermediate by using continuous flow micro-channel reactor

The invention discloses a process method for preparing (2 'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidyl-3 ', 5 '-dibenzoate, and belongs to the technical field of organic synthesis application, the process method is a novel process method for preparing a target product within reaction time of dozens of seconds from (2R, 3R, 4R, 5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methyl benzoate as a raw material in a continuous flow micro-channel reactor and stannic chloride as a catalyst by introducing materials into the reactor through a counting pump, heating, mixing andreacting to obtain a product; the method has the characteristics of simplicity and safety in operation, high yield and short reaction time, and can realize continuous production; the yield of the product is 55% or above, and the purity reaches 99%.

A preparation process of rope non-cloth wei improved method

The invention provides a method for improving technique of rope non-cloth wei, for the oxidation of olefinic bond when [...], the oxidizing agent is potassium permanganate into sodium permanganate, product yield from 78% improved to 90% or more; in cytosine with halo ethylthio butt coupling reaction using tin tetrachloride to replace the zinc chloride catalytic, yield from 75% to a 88%; using five fluoro phenol instead of the nitro phenol to prepare phosphoric acid ester side chain, so that the phosphoric acid ester side chain of the yield from 80% up to 95%.

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

Technology for preparing sofosbuvir intermediate

A technology for preparing a sofosbuvir intermediate represented by formula 1 comprises the following steps: (a) reducing a compound 2 by sodium borohydride to generate a compound 3; (b) reacting thecompound 3 with a methanol-hydrochloric acid solution to generate a compound 4; (c) carrying out a fluorination reaction on the compound 4 and a fluorination reagent in a reaction solvent at -10 to -65 DEG C under the protection of nitrogen, and post-treating a reaction solution after the reaction is fully carried out in order to obtain a compound 5; (d) cooling an n-hexane or petroleum ether or cyclohexane solution of the compound 5 to -5-5 DEG C under the protection of nitrogen, adding thionyl chloride, slowly dropwise adding methanol or ethanol at a controlled temperature of -5-5 DEG C, rising the temperature to 10-40 DEG C after the dropwise addition, continuously performing stirring until the reaction is completed , and removing the solvent to obtain a compound 6; and (e) condensing the compound 6 and a compound 7, and carrying out hydrolysis treatment to obtain the target product which is the compound 1. The preparation technology has the characteristics of high yield, convenience and safety in operation, less discharge of three wastes, low production cost, and suitableness for industrial production.

Synthesis method of sofosbuvir

The invention provides a synthesis method of sofosbuvir. The synthesis method of the sofosbuvir comprises the following steps: performing mitsunobu reaction on ((2R,3R,4R)-3-benzoyloxy)-4-fluorine-5-hydroxyl-4-methyltetrahydrofuran-2-yl)methyl benzoate to produce sulfonate to obtain a compound 1; abutting the compound 1 and N-benzoylcytosine to produce a compound 2. The method adopts mitsunobu reaction to avoid production of an isomer, and the isomer is reduced to 5 percent or below; according to the method, sulfonate and N-benzoylcytosine are abutted, so the use ofa stannic chloride raw material is avoided; furthermore, the yield is high and few solid waste is generated during aftertreatment, so that the method is suitable for large-scale industrialized production.

Intermediate compound for synthesis of sofosbuvir and synthetic method thereof

The invention discloses an intermediate compound for synthesis of sofosbuvir and a synthetic method thereof; the intermediate compound comprises 4 intermediate products and 1 target compound, wherein the 4 intermediate products include methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl) benzoate, methyl ((2R,3R,4R)-3-(benzoyloxy)-4-fluoro-5-chloro-4-methyltetrahydrofuran-2-yl) benzoate, (2'R)-N-benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine 3',5'-dibenzoate, and ((2R,3R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-methyltetrahydrofuran-2-yl) methyl benzoic acid, and the target compound is (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine. Compared with existing synthetic methods, the synthetic method has high content of target compound and has little impurities generated in the synthetic process; the results of the synthetic method are stable, the synthetic method is simple to perform and is applicable to large-scale industrial production and technical popularization.

Preparation method for hepatitis C virus resisting drug sofosbuvir intermediates

The invention relates to a preparation method for sofosbuvir intermediates 9, 11. The preparation method comprises the following steps: by taking a compound I as an initial material, carrying out an additive reaction with electrophilic reagents acrylonitrile, cyanoacetylene, propargyl ester and acrylate and carrying out ring-closing reaction to prepare corresponding intermediates (VII, V, IV and II); carrying out a ring-opening reaction on the intermediates (VII, V, IV and II) and a fluorination reagent to obtain corresponding intermediates (VIII, VI, II and III), carrying out a reaction on the intermediate VIII and benzoyl chloride in an alkaline condition to prepare an intermediate IX, and further carrying out dehydrogenation reaction on the intermediate IX in the presence of an oxidizing agent to prepare an intermediate 9; carrying out a reaction on the intermediate VI and benzoyl chloride in the alkaline reaction to prepare the intermediate 9; and further carrying out dehydrogenation reaction on the intermediate III in the presence of an oxidizing agent to prepare the intermediate 11.

A nucleoside phosphoramide prodrug and its preparation method and its application

The invention relates to a nucleoside phosphamide prodrug as well as a preparation method and application of the nucleoside phosphamide prodrug. The nucleoside phosphamide prodrug is selected from any one of a compound I and a compound II, wherein in the formulas of the compound I and the compound II, X is selected from any one of F, Cl, Br and I. Compared with GS7977andGS7851, The compound I or II disclosed by the invention has more excellent resistance to hepatitis C virus, wherein the formulas I and II are respectively as shown in specifications.

Preparation method of sofosbuvir intermediate or derivative thereof

The invention discloses a preparation method of a sofosbuvir intermediate or a derivative thereof. Compounds represented by formula 3 and formula 6 react with an alkali catalyst DBU or DMAP at 20-70DEG C to prepare a compound represented by formula 1. The method is simple to operate, and is suitable for industrial production.