(2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol

Base Information

• Chemical Name: (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol
• CAS No.: 114748-62-8
• Molecular Formula: C₃₂H₃₁N₃O₄S
• Molecular Weight: 553.682
• Mol file: 114748-62-8.mol

Synonyms:(2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol

Chemical Property of (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol

There total 3 articles about (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol 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: 94.0%

7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin (98891-39-5) + trityl chloride (76-83-5) → (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol (114748-62-8)

Guidance literature:

With dmap; triethylamine; In pyridine; at 65 ℃; for 16.5h;

DOI:10.1016/S0040-4039(00)80417-7

Reference yield:

4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (29877-76-7) → (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol (114748-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH; 2.) Rexyn^TM201 strongly basic ion exchange resin (hydroxide form) / 1.) CH₃CN, RT, 45 min; 2.) MeOH, reflux, 1.5 h

2: 94 percent / DMAP, Et₃N / pyridine / 16.5 h / 65 °C

With dmap; Rexyn^TM201 strongly basic ion exchange resin (hydroxide form); sodium hydride; triethylamine; In pyridine;

DOI:10.1016/S0040-4039(00)80417-7

Reference yield:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → (2R,3S,5R)-5-(4-Methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-ol (114748-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH; 2.) Rexyn^TM201 strongly basic ion exchange resin (hydroxide form) / 1.) CH₃CN, RT, 45 min; 2.) MeOH, reflux, 1.5 h

2: 94 percent / DMAP, Et₃N / pyridine / 16.5 h / 65 °C

With dmap; Rexyn^TM201 strongly basic ion exchange resin (hydroxide form); sodium hydride; triethylamine; In pyridine;

DOI:10.1016/S0040-4039(00)80417-7

upstream raw materials:

7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin

trityl chloride

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

Downstream raw materials:

Thiocarbonic acid O-[(2R,3S,5R)-5-(4-methoxy-2-methylsulfanyl-pyrrolo[2,3-d]pyrimidin-7-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl] ester O-phenyl ester

7-iodo-2',3'-dideoxy-7-deazaguanosine

2-Amino-5-iodo-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one

5-Iodo-2-methylsulfanyl-7-((2R,5S)-5-trityloxymethyl-tetrahydro-furan-2-yl)-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one