9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine

Base Information

• Chemical Name: 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine
• CAS No.: 125084-69-7
• Molecular Formula: C₃₄H₃₇BrN₆O₄Si
• Molecular Weight: 701.695
• Mol file: 125084-69-7.mol

Synonyms:9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine

Chemical Property of 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine

There total 8 articles about 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine 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: 97.0%

9-<3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine (125084-68-6) + benzyl isothiocyanate (3173-56-6) → 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine (125084-69-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; acetonitrile; at 35 ℃; for 15h;

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine (125084-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / 12 h / 20 °C

2: 95 percent / Me₂BBr; Et₃N / CH₂Cl₂ / 1 h / -78 °C

3: 89 percent / Et₃N / tetrahydrofuran; acetonitrile / 48 h / 20 °C

With dimethylboron bromide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;

DOI:10.1021/jo010935d

Reference yield:

adenosine (58-61-7) → 9-<2-O-<(benzylamino)carbonyl>-3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine (125084-69-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) α-acetoxyisobutyryl bromide; 2.) Dowex 1x2 (OH^-) resin / 1.) MeCN/H2O, RT, 1 h; 2.) MeOH, RT, 15 min

2: 87 percent / pyridine / 16 h / Ambient temperature

3: 90 percent / Et₃N, (CH₃)2BBr / CH₂Cl₂ / 0.25 h / -78 °C

4: 93 percent / Et₃N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature

With pyridine; dimethylboron bromide; Dowex 1x2 (OH^-) resin; acetoxyisobutyryl bromide; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

upstream raw materials:

9-<3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine

benzyl isothiocyanate

(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuran-3-yl acetate

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

Downstream raw materials:

(3aR,4S,6R,6aR)-6-(6-amino-9H-purin-9-yl)-3-benzyl-4-((tert-butyldiphenylsilyloxy)methyl)tetrahydrofuro[3,4-d]oxazol-2(3H)-one

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine

9-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]adenine

3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine