(2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• CAS No.: 84765-97-9
• Molecular Formula: C₁₆H₂₂N₄O₄
• Molecular Weight: 334.375

Synonyms:(2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Chemical Property of (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Chemical Property:

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Technology Process of (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

There total 5 articles about (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)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: 50.0%

1-bromocyclohexane (108-85-0) + 6-Chloropurine riboside (2004-06-0) → (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (84765-97-9)

Guidance literature:

With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; sodium carbonate; In N,N-dimethyl-formamide; for 4h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/acsmedchemlett.0c00673

Reference yield:

cyclohexylmagnesium bromide (931-50-0) → (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (84765-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloro<1,3-bis(diphenylphosphine)propane>nickel(II) / diethyl ether / Ambient temperature

2: nBu₄F / tetrahydrofuran / 4 h / 0 °C

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(00)88701-8

Reference yield:

9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-cyclohexyl-9H-purine → (2R,3R,4S,5R)-2-(6-cyclohexyl-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (84765-97-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h; Yield given;

DOI:10.1016/S0040-4039(00)88701-8

upstream raw materials:

6-chloro-9-(2,3,5-tris-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-9H-purine

cyclohexylmagnesium bromide

Cyclohexanecarboxylic acid

1-bromocyclohexane

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