6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine

Base Information

• Chemical Name: 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine
• CAS No.: 222296-27-7
• Molecular Formula: C₄₅H₅₃N₅O₆Si
• Molecular Weight: 788.031
• Mol file: 222296-27-7.mol

Synonyms:6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine

Chemical Property of 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine

There total 7 articles about 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine 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:

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose (150370-50-6) + 6-chloro- 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine (222296-31-3) → 6-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosylamono)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine + 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine (222296-27-7)

Guidance literature:

With rac-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In toluene; at 130 ℃; for 0.5h; Title compound not separated from byproducts.;

DOI:10.1021/jo010925c

Reference yield:

2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-69-5,94943-10-9,83462-68-4) → 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine (222296-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / TMSN₃; SnCl₄ / CH₂Cl₂ / 30 h / 20 °C

2: 79 percent / H₂ / Lindlar catalyst / ethanol / 3 h / 20 °C / 760.05 Torr

3: tBuONa; (-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / Pd₂(dibenzylideneacetone)3 / toluene / 0.5 h / 130 °C

With rac-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; trimethylsilylazide; hydrogen; tin(IV) chloride; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Lindlar's catalyst; In ethanol; dichloromethane; toluene;

DOI:10.1021/jo010925c

Reference yield:

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 6-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosylamino)-9-(2-(trimethylsilyl)-ethoxymethyl)-purine (222296-27-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / iPr₂NEt / dimethylformamide / 0.25 h / 20 °C

2: tBuONa; (-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / Pd₂(dibenzylideneacetone)3 / toluene / 0.5 h / 130 °C

With rac-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo010925c

upstream raw materials:

1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-mannopyranose

6-chloro- 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

(2-trimethylethylsilylethoxy)methyl chloride

2,3,4,6-tetra-O-benzyl-1-O-acetyl-α-D-mannopyranose