[(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester

Base Information

• Chemical Name: [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester
• CAS No.: 193894-19-8
• Molecular Formula: C₂₉H₃₆N₆O₇SSi
• Molecular Weight: 640.792

Synonyms:

Chemical Property of [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester

There total 5 articles about [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester 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: 82.0%

1,3,2-benzdioxathiole-2,2-dioxide (4074-55-9) + N-[9-[(2R,4S,5R)-5-(aminomethyl)-4-[tert-butyl(dimethyl)silyl]oxytetrahydrofuran-2-yl]purin-6-yl]benzamide 4-methylbenzenesulfonic acid (139063-20-0) → [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester (193894-19-8)

Guidance literature:

With triethylamine;

DOI:10.1016/S0040-4039(97)01179-9 DOI:10.1016/S0040-4020(97)10421-5

Reference yield:

N6-benzoyl-2'-deoxyadenosine (4546-72-9) → [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester (193894-19-8)

Guidance literature:

Multi-step reaction with 4 steps

1: PPh₃, CBr₄, NaN₃ / dimethylformamide

2: Et₃N

3: H₂ / 10 percent Pd-C

4: 82 percent / Et₃N

With sodium azide; carbon tetrabromide; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)01179-9

Reference yield:

5'-azido-N6-benzoyl-2',5'-dideoxy-adenosine (74625-78-8) → [(2R,3S,5R)-5-(6-Benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-sulfamic acid 2-hydroxy-phenyl ester (193894-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N

2: H₂ / 10 percent Pd-C

3: 82 percent / Et₃N

With hydrogen; triethylamine; palladium on activated charcoal;

DOI:10.1016/S0040-4039(97)01179-9

upstream raw materials:

1,3,2-benzdioxathiole-2,2-dioxide

N-[9-[(2R,4S,5R)-5-(aminomethyl)-4-[tert-butyl(dimethyl)silyl]oxytetrahydrofuran-2-yl]purin-6-yl]benzamide 4-methylbenzenesulfonic acid

5'-azido-N⁶-benzoyl-2',5'-dideoxy-adenosine

tert-butyldimethylsilyl chloride

Downstream raw materials:

C₂₇H₃₁N₉O₉S

5'-O-(4,4'-dimethoxytrityl)-3'-deoxythymidinylsulfamido-(3'(N)->5'(N))-N⁶-benzoyl-5',2'-dideoxyadenosine

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