(2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Base Information

• Chemical Name: (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 104291-20-5
• Molecular Formula: C₂₇H₂₅ClN₄O₅
• Molecular Weight: 520.972
• Mol file: 104291-20-5.mol

Synonyms:(2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property of (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate

There total 7 articles about (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 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: 76.0%

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride (3056-12-0,3601-89-6,4330-21-6,52304-86-6,141846-57-3) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (104291-20-5)

Guidance literature:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine; With potassium hydroxide; In acetonitrile; at 20 ℃; for 0.0833333h;

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride; In acetonitrile; at 20 ℃; for 0.333333h;

DOI:10.1016/j.tet.2013.11.048

Reference yield: 45.0%

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (52162-55-7,69256-45-7,61826-14-0) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 2-Amino-4-chlor-7-<2-desoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidin (104291-22-7) + 2-Amino-4-chlor-7-<2-desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-7H-pyrrolo<2,3-d>pyrimidin (104291-20-5)

Guidance literature:

With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 0.166667h;

Reference yield:

Hoffer's chlorosugar (3601-89-6,4330-21-6,52304-86-6,3056-12-0,141846-57-3) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → (2R,3S,5R)-5-(2-amino-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (104291-20-5)

Guidance literature:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine; With Tris(3,6-dioxaheptyl)amine; potassium hydroxide; In acetonitrile; at 20 ℃; for 0.0833333h;

Hoffer's chlorosugar; In acetonitrile; at 20 ℃; for 0.666667h;

upstream raw materials:

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

D-2-deoxyribose

1-O-methyl-2-deoxy-D-ribofuranoside

Downstream raw materials:

2-amino-4-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

(2R,3S,5R)-5-(2,4-diamino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate

7-(2-deoxy-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate