Remdesivir

Base Information

• Chemical Name: Remdesivir
• CAS No.: 1809249-37-3
• Molecular Formula: C27H35N6O8P
• Molecular Weight: 602.584
• Mol file: 1809249-37-3.mol

Synonyms:

Chemical Property of Remdesivir

Chemical Property:

• PSA: 213.36000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 3.28428

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Remdesivir

There total 82 articles about Remdesivir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

2-ethylbutyl (2S)-2-{[(S)-{[(3aR,4R,6R,6aR)-6-{4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}-6-cyano-2-phenyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methoxy}(phenoxy)phosphoryl]amino}propanoate → (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 (1809249-37-3,1911578-75-0)

Guidance literature:

at 60 ℃;

Reference yield: 81.0%

(2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile (1191237-69-0) + C19H27N2O7P → (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 (1809249-37-3,1911578-75-0)

Guidance literature:

With diisopropylamine; zinc dibromide; In tetrahydrofuran; at 20 ℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere; Molecular sieve;

Reference yield:

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) → (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 (1809249-37-3,1911578-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: acetic anhydride; dimethyl sulfoxide / 48 h / 20 °C / Inert atmosphere

2.1: chloro-trimethyl-silane / tetrahydrofuran / 0.33 h / 20 °C / Inert atmosphere

2.2: 0.17 h / -78 °C / Inert atmosphere

3.1: dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: boron trichloride / dichloromethane / 1 h / -78 - -20 °C / Inert atmosphere

5.1: tert-butylmagnesium chloride / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

With chloro-trimethyl-silane; tert-butylmagnesium chloride; acetic anhydride; boron trichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(2S)-2-ethylbutyl 2-(((S)-(perfluorophenoxy)(phenoxy)phosphoryl)amino)propanoate

(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

(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

(2R,3R,4S,5R)?2?(4?aminopyrrolo[1,2?f][1,2,4]triazin?7?yl)?3,4?dihydroxy?5?(hydroxymethyl)tetrahydrofuran?2?carbonitrile

Downstream raw materials:

GS-704277

Refernces

• 1、 Gannedi, Veeranjaneyulu,Villuri, Bharath Kumar,Reddy, Sivakumar N.,Ku, Chiao-Chu,Wong, Chi-Huey,Hung, Shang-Cheng. "Practical Remdesivir Synthesis through One-Pot Organocatalyzed Asymmetric (S)-P-Phosphoramidation". . p. 4977 - 4985. Retrieved 2021/04/02.
• 2、 -. "N-protected heterocyclic compound, preparation method thereof and method for preparing C-nucleoside derivative by using N-protected heterocyclic compound". Paragraph 0469; 0470; 0471. . Retrieved 2021/08/14.