(-)-9-pseudo-β-L-idopyranosyladenine

Base Information

• Chemical Name: (-)-9-pseudo-β-L-idopyranosyladenine
• CAS No.: 121239-62-1
• Molecular Formula: C₁₂H₁₇N₅O₄
• Molecular Weight: 295.298
• Mol file: 121239-62-1.mol

Synonyms:

Chemical Property of (-)-9-pseudo-β-L-idopyranosyladenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-9-pseudo-β-L-idopyranosyladenine

There total 15 articles about (-)-9-pseudo-β-L-idopyranosyladenine 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: 92.0%

(1R,2S,3S,4R,6R)-4-(6-Amino-purin-9-yl)-2-benzyloxy-6-hydroxymethyl-cyclohexane-1,3-diol (121239-64-3) → (-)-9-pseudo-β-D-glucopyranosyladenine (121239-62-1,121312-63-8)

Guidance literature:

With sodium; In tetrahydrofuran; ammonia; at -78 ℃; for 0.5h;

DOI:10.1248/cpb.37.542

Reference yield:

(1R,2S,3S,4S,6S)-4-(6-Amino-purin-9-yl)-2-benzyloxy-6-hydroxymethyl-cyclohexane-1,3-diol (121239-64-3) → (-)-9-pseudo-β-L-idopyranosyladenine (121239-62-1,121312-63-8)

Guidance literature:

With sodium; In tetrahydrofuran; ammonia; at -78 ℃; for 0.5h; Yield given;

DOI:10.1248/cpb.37.542

Reference yield:

Acetic acid (1R,2S,5S,6R)-5-acetoxy-2-acetoxymethyl-6-benzyloxy-3-nitro-cyclohex-3-enyl ester (121239-65-4) → (-)-9-pseudo-β-L-idopyranosyladenine (121239-62-1,121312-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / KF / 18-crown-6 / dimethylformamide / 1 h / 2 °C

2: 77 percent / (n-Bu)3SnH, α,α'-azobis-iso-butyronitrile / benzene / 3 h / 80 °C

3: 1 percent NaOMe / methanol / 8 h / 23 °C

4: Na / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C

With potassium fluoride; azobisisobutyronitrile; tri-n-butyl-tin hydride; sodium methylate; sodium; 18-crown-6 ether; In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.37.542

upstream raw materials:

(1R,2S,3S,4R,6R)-4-(6-Amino-purin-9-yl)-2-benzyloxy-6-hydroxymethyl-cyclohexane-1,3-diol

(1R,2S,3S,4R,6R)-4-(5-Amino-6-chloro-pyrimidin-4-ylamino)-2-benzyloxy-6-hydroxymethyl-cyclohexane-1,3-diol

Benzoic acid (1R,2R,3S,4S,5R)-2,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-3-benzyloxy-cyclohexylmethyl ester

Benzoic acid (1R,2R,3S,4S,5R,6S)-2,4-diacetoxy-5-(6-benzoylamino-purin-9-yl)-3-benzyloxy-6-nitro-cyclohexylmethyl ester