9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine

Base Information

• Chemical Name: 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine
• CAS No.: 358359-65-6
• Molecular Formula: C₃₁H₂₈Cl₂N₄O₃S
• Molecular Weight: 607.56
• Mol file: 358359-65-6.mol

Synonyms:9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine

Chemical Property of 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine

There total 6 articles about 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine 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: 30.0%

2,6 dichloropurine (5451-40-1) + 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-xylofuranose (358359-63-4) → 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine (358359-65-6) + 9-(2,3,5-tri-O-benzyl-4-thio-β-L-xylofuranosyl)-2,6-dichloropurine (358359-66-7)

Guidance literature:

With tin(IV) chloride; In acetonitrile;

DOI:10.1081/NCN-100002420

Reference yield:

(2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran (89824-86-2) → 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine (358359-65-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 48 percent / stannic chloride / CH₂Cl₂ / 20 °C

2: 60 percent / triphenylphosphine; iodine; imidazole / toluene; acetonitrile / 24 h / 90 °C

3: 77 percent / acetic acid / 2 h / 20 °C

4: 30 percent / stannic chloride / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; iodine; tin(IV) chloride; acetic acid; triphenylphosphine; In dichloromethane; toluene; acetonitrile;

DOI:10.1080/15257770500269077

Reference yield:

benzyl 2,3,5-tri-O-benzyl-1,4-dithio-L-xylofuranoside (378791-96-9) → 9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-2,6-dichloropurine (358359-65-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / acetic acid / 2 h / 20 °C

2: 30 percent / stannic chloride / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

With tin(IV) chloride; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1080/15257770500269077

upstream raw materials:

2,6 dichloropurine

1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-xylofuranose

D-Arabinose

methyl D-arabinofuranoside

Downstream raw materials:

9-((2R,3S,4S,5S)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-2-chloro-9H-purin-6-ylamine

2,6-Diazido-9-((2R,3S,4S,5S)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-9H-purine

9-(2,3,5-tri-O-benzyl-4-thio-α-L-xylofuranosyl)-9H-purine-2,6-diamine