N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

Base Information

• Chemical Name: N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide
• CAS No.: 153764-74-0
• Molecular Formula: C₂₆H₃₇N₅O₄Si
• Molecular Weight: 511.696
• Mol file: 153764-74-0.mol

Synonyms:

Chemical Property of N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide

There total 4 articles about N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide 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: 62.0%

methylmagnesium bromide (75-16-1) + N-(9-{(2R,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-oxo-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide → N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (153764-74-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)96259-3

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (153764-74-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / pyridine / 20 h / Ambient temperature

2: 1.) pyridine 2.) NaOH / 1.) r.t., 5 h, 2.) H₂O-EtOH-pyridine, 0 deg C, 20 min

3: 74 percent / DCC, Cl₂CHCO₂H / dimethylsulfoxide / 1 h / 0 - 20 °C

4: 62 percent / tetrahydrofuran / 2.5 h / -78 °C

With pyridine; dichloro-acetic acid; sodium hydroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)96259-3

Reference yield:

(2R,3R,5S)-2-(6-Amino-purin-9-yl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-3-ol (153764-71-7) → N-(9-{(2R,3S,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-3-methyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (153764-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pyridine 2.) NaOH / 1.) r.t., 5 h, 2.) H₂O-EtOH-pyridine, 0 deg C, 20 min

2: 74 percent / DCC, Cl₂CHCO₂H / dimethylsulfoxide / 1 h / 0 - 20 °C

3: 62 percent / tetrahydrofuran / 2.5 h / -78 °C

With pyridine; dichloro-acetic acid; sodium hydroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)96259-3

upstream raw materials:

methylmagnesium bromide

chlorodimethyl(1,1,2-trimethylpropyl)silane

(2R,3R,5S)-2-(6-Amino-purin-9-yl)-5-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-tetrahydro-furan-3-ol

N-(9-{(2R,3R,5S)-5-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-hydroxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide