(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

Base Information

• Chemical Name: (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
• CAS No.: 1369903-46-7
• Molecular Formula: C₃₃H₃₁N₅O₄
• Molecular Weight: 561.64
• Mol file: 1369903-46-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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: 78.0%

trimethylsilyl cyanide (7677-24-9) + (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 (1355049-94-3) → (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 (1355357-49-1) + (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 (1369903-46-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In dichloromethane; at -30 ℃; Reagent/catalyst; Temperature; diastereoselective reaction; Flow reactor; Industrial scale;

DOI:10.1021/acs.oprd.0c00172

Reference yield: 39.6%

trimethylsilyl cyanide (7677-24-9) + (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 (1355049-94-3) → (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 (1369903-46-7)

Guidance literature:

(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; With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.5h; Inert atmosphere;

trimethylsilyl cyanide; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

Reference yield:

7-iodopyrrolo-[2,1-f][1,2,4]-triazin-4-amine (1770840-43-1) + (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one (14233-64-8,134307-32-7,55094-52-5) → (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 (1369903-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloro-trimethyl-silane / tetrahydrofuran / 0.5 h / 0 °C

1.2: 0.5 h / -10 °C

2.1: trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid / dichloromethane / -30 °C / Flow reactor; Industrial scale

With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.oprd.0c00172

upstream raw materials:

7-bromo-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

trimethylsilyl cyanide

(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)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

Downstream raw materials:

C₂₇H₃₅N₆O₈P