(1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine

Base Information

• Chemical Name: (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine
• CAS No.: 262372-02-1
• Molecular Formula: C₁₂H₁₅N₅O₃
• Molecular Weight: 277.283
• Mol file: 262372-02-1.mol

Synonyms:(1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine

Chemical Property of (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine

There total 13 articles about (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine 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:

9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine (262372-06-5) → (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine (262372-02-1)

Guidance literature:

With trifluoroacetic acid; In water;

DOI:10.1081/NCN-100002360

Reference yield:

6-chloro-9-(2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-7-yl)-9H-purin-2-ylamine → (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine (262372-02-1)

Guidance literature:

With trifluoroacetic acid; In water; at 20 ℃; for 48h;

DOI:10.1021/jo015924z

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → (1S,4R,5S)-9-(5-hydroxy-4-hydroxymethyl-2-cyclohexen-1-yl)guanine (262372-02-1)

Guidance literature:

Multi-step reaction with 2 steps

1: PPh₃; DEAD / dioxane / 20 °C

2: TFA / H₂O / 48 h / 20 °C

With triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In 1,4-dioxane; water; 1: Mitsunobu reaction;

DOI:10.1021/jo015924z

upstream raw materials:

9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine

2-Amino-6-chloropurin

(4aR,7R,8aS)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-7-ol

(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one

Downstream raw materials:

N-[9-(5-hydroxy-4-hydroxymethyl-cyclohex-2-enyl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-isobutyramide

N-(9-{5-hydroxy-4-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-cyclohex-2-enyl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-isobutyramide