(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol
• CAS No.: 2040291-27-6
• Molecular Formula: C₁₇H₁₈N₄O₄
• Molecular Weight: 342.354

Synonyms:

Chemical Property of (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

LLY-283 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: LLY-283 is an inhibitor of protein arginine methyltransferase 5 (PRMT5; IC50 = 22 nM). It is selective for PRMT5 over a panel of methyltransferases, including PRMT4, -6, and -7 at 1 μM. It reduces symmetric demethylation of SmBB'' in MCF-7 cells (IC50 = 25 nM) and inhibits proliferation of various breast, gastric, hematological, lung, skin, and ovarian cancer cell lines (IC50s = 3-30 nM). LLY-283 (20 mg/kg) inhibits tumor growth in an A375 mouse xenograft model. It also disrupts alternative splicing events in, and inhibits proliferation and self-renewal of, patient-derived glioblastoma stem cells and increases survival in an orthotopic patient-derived xenograft (PDX) mouse model. See the Structural Genomics Consortium (SGC) website for more information.

Technology Process of (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol

There total 16 articles about (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol 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: 74.0%

(R)-[(3aR,4R,6R,6aR)-4-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-phenylmethanol → (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((R)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol (2040291-27-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 0.75h;

Reference yield: 71.4%

C20H22N4O4 → (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((S)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol (2040291-27-6)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 12h;

DOI:10.1021/acsmedchemlett.8b00014

Reference yield:

C21H19F3N6O7S → (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((R)-hydroxy(phenyl)methyl)tetrahydrofuran-3,4-diol (2040291-27-6)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In methanol; at 50 ℃; for 6h; under 760.051 Torr;

DOI:10.1002/asia.202001090

upstream raw materials:

[(3aR,4R,6R,6aR)-4-(4-chloropyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol

4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidine

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