1355049-94-3

Usage

Uses

Used in Medicinal Chemistry:
(3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol is used as a potential pharmaceutical candidate for the development of new drugs. Its unique structure and functional groups may allow for targeted interactions with biological targets, such as enzymes or receptors, which could lead to the discovery of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (3R,4R,5R)-2-(4-aminopyrrole-[2,1-f][1,2,4]-triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-ol serves as a valuable intermediate or building block for the synthesis of more complex molecules. Its versatile structure and the presence of multiple functional groups make it a useful component in the construction of a wide range of organic compounds, including natural products, pharmaceuticals, and materials with specific properties.

Upstream product

• 937046-98-5 7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine 
• 14233-64-8 (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one 
• 159326-68-8 pyrrolo[2,1-f][1,2,4]triazin-4-amine 
• 532-20-7 D-Ribose 
• 100-39-0 benzyl bromide 
• 1770840-43-1 7-iodopyrrolo-[2,1-f][1,2,4]-triazin-4-amine 
• 100-59-4 phenylmagnesium chloride 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 

Downstream Products

• 158227-80-6 7-((2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran-2-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine 
• 1355357-49-1 (2R,3R,4R,5R)‐2‐{4‐aminopyrrolo[2,1‐f][1,2,4]triazin‐7‐yl}‐3,4‐bis(benzyloxy)‐5‐[(benzyloxy)methyl]tetrahydrofuran‐2‐carbonitrile 
• 1369903-46-7 (2S,3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-carbonitrile 
• 1355050-18-8 C₃₃H₃₄N₄O₄ 
• 1191237-70-3 C₃₃H₃₄N₄O₄ 
• 1355357-50-4 C₃₅H₃₆N₄O₄ 
• 1191237-68-9 (3R,4R,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-bis(benzyloxy)-5-((benzyloxy) methyl)tetrahydrofuran-2-carbonitrile 
• 1355050-10-0 (2S)-isopropyl 2-(((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1355050-16-6 C₃₄H₃₂N₄O₄ 
• 1191237-69-0 (2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile 
• 1355049-95-4 (2S,3R,4S,5R)-2-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-carbonitrile 
• 1355050-11-1 (2S)-2-ethylbutyl 2-(((((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1911578-75-0 (2S)-2-ethylbutyl 2-(((R)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 
• 1809249-37-3 (2S)-2-ethylbutyl 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5-cyano-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)amino)propanoate 

Relevant academic research and scientific papers

Continuous Flow C-Glycosylation via Metal-Halogen Exchange: Process Understanding and Improvements toward Efficient Manufacturing of Remdesivir

As remdesivir is the first approved treatment for COVID-19 (SARS-CoV-2), its production is likely to be of vital importance in the near future. Continuous flow processing has been demonstrated as a key technology in the manufacturing of high-volume active pharmaceutical ingredients and is considered for use in this synthetic sequence. In particular, the challenging C-glycosylation of a pyrrolotriazinamine via metal-halogen exchange was identified as a transformation with significant potential benefit, as exemplified by calorimetric analysis of each reaction step. Multiple simplifications of this process were attempted in batch but in general were found to be unfruitful. The five-feed process was then transferred to a flow setup, where specific conditions were found to circumvent solid formation and permit stable processing. Detailed optimization of stoichiometries provided an improvement upon batch conditions with a total residence time of 1 min.

Improvement of the C-glycosylation Step for the Synthesis of Remdesivir

The bulk supply of the antiviral C-nucleoside analogue remdesivir is largely hampered by a low-yielding C-glycosylation step in which the base is coupled to the pentose unit. Here, we disclose a significantly improved methodology for this critical transfo

Development of a Large-Scale Cyanation Process Using Continuous Flow Chemistry en Route to the Synthesis of Remdesivir

The implementation of cyanation chemistry at manufacturing scales using batch equipment can be challenging because of the hazardous nature of the reagents employed and the tight control of reaction parameters, including cryogenic temperatures, that help t

REMDESIVIR INTERMEDIATES

The present invention relates to a process for the preparation of a compound of formula (I) and to novel intermediates of the synthesis, wherein X is hydrogen, bromine or iodine; R1 is a protecting group, R2 is hydrogen or a protecting group, and PG is a protecting group.

Preparation method of ribonucleoside

The invention provides a method for preparing ribonucleoside of a formula I, which comprises the following steps: forming a reaction mixture containing a deprotonation reagent, a coupling agent, a silylation reagent, a compound of a formula II and a compound of a formula III under conditions suitable for preparing the formula I, wherein a hydroxyl protecting group PG is an independent hydroxyl protecting group. According to the technical scheme provided by the invention, the defects of long reaction steps, low reaction yield, high preparation cost, complex post-treatment process and unsuitability for industrial large-scale preparation in the existing preparation method of the formula (I) are overcome, and a preparation method for directly synthesizing the formula (I) from the formula (II) in one step is provided. The method has few steps, high yield, simple and convenient operation and low cost, and the method is suitable for industrial large-scale production.

Compound containing guanidyl group, and preparation method and application thereof

The invention provides a preparation containing a guanidino compound and used for treating pneumoviridae virus infection, a method, a compound of a formula I, and a method and an intermediate for synthesizing the compound of the formula I.

Intermediate of and preparation method thereof

The present invention provides an intermediate of Remdesivir and a preparation method therefor. The preparation method has the advantages of low costs, high yield, good product purity, etc. , and can achieve the efficient synthesis of Remdesivir. In each formula, R1, R2, R3, R4, R5, R8, PG and X are as defined in the description.

METHODS OF PREPARING 1'-CYANO NUCLEOSIDES

The present disclosure generally describes methods of preparing l'-cyano nucleosides, such as a compound of Formula (I). For example, the compound of Formula (I) can be prepared from a compound of Formula (Il-a) in a flow reactor.

Synthesis method of key intermediate of ridecevir

The invention provides a novel method for preparing a key intermediate of ridecevir as shown in a formula (VII). Benzyl fully-protected lactone as shown in a formula (I) is used as a starting material and is subjected to ring opening to obtain a compound as shown in a formula (II). The hydroxyl of the compound (II) is protected by a proper protecting group to obtain the compound shown in the formula (III). The compound (III) and the compound (IV) are subjected to coupling, protecting group removal and cyclization to obtain an intermediate shown as a formula (V) by a one-pot method. The intermediate (V) is subjected to two-step conversion to obtain the key intermediate (VII) of the ridecevir. According to the method provided by the invention, the compound (I) which can be bought in the market is used as the starting material, and the key intermediate compound (VII) for preparing the ridecevir is obtained at high yield through five-step reaction, so that the cost is greatly reduced, and the method is suitable for industrial mass production.

Preparation method of ridecevir intermediate

The invention discloses a preparation method of a ridecevir intermediate. The preparation method comprises the following steps: firstly, reacting 7-iodopyrrolo [2, 1-f] [1, 2, 4] triazine 4-amine with N, N-dimethylformamide dimethyl acetal, then adding i-PrMgCl or butyl lithium into the product obtained in the previous step for reacting, then adding 2, 3, 5-tribenzyloxy-D-ribonucleic acid 1, 4-lactone, and finally removing a protecting group to obtain the remdesivir intermediate 1-C-(4-aminopyrrole [2, 1-f] [1, 2, 4] triazine-7-yl)-2, 3, 5-trioxy-(benzyl)-D-ribose furanose. According to the preparation method of the ridecevir intermediate, a mature product in the current market is selected as a reactant, the raw materials are easy to obtain, and the production cost is reduced; and the method has the advantages of simple process, short time consumption, high production efficiency, high yield, mild reaction conditions and simple and convenient post-treatment, is suitable for large-scale preparation, and has great application prospects.