(2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol
• CAS No.: 131265-32-2
• Molecular Formula: C₂₃H₃₃N₅O₅Si
• Molecular Weight: 487.631
• Mol file: 131265-32-2.mol

Synonyms:

Chemical Property of (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol

There total 3 articles about (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-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:

8-bromoadenosine (2946-39-6) → (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol (131265-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Na / 1.) DMF, 2.) 80 deg C, 1.5 h

2: N,N-dimethylaminopyridine, NEt₃ / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

With dmap; sodium; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1990-27066

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol (131265-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Na / 1.) DMF, 2.) 80 deg C, 1.5 h

2: N,N-dimethylaminopyridine, NEt₃ / dimethylformamide; CH₂Cl₂ / 12 h / Ambient temperature

With dmap; sodium; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1990-27066

Reference yield:

8-Benzyloxyadenosine (131265-29-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3R,4S,5R)-2-(6-Amino-8-benzyloxy-purin-9-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3,4-diol (131265-32-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide; for 12h; Yield given; Ambient temperature;

DOI:10.1055/s-1990-27066

upstream raw materials:

8-Benzyloxyadenosine

tert-butyldimethylsilyl chloride

8-bromoadenosine

benzyl alcohol

Downstream raw materials:

(3aR,4R,6R,6aR)-4-(6-Amino-8-benzyloxy-purin-9-yl)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxole-2-thione

8-Benzyloxy-2',3'-dideoxyadenosine

8-Benzyloxy-5'-O-tert-butyldimethylsilyl-2',3'-dideoxyadenosine

(2R,3S,5R)-5-(6-Amino-8-benzyloxy-purin-9-yl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-ol