(S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate

Base Information

• Chemical Name: (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate
• CAS No.: 872025-83-7
• Molecular Formula: C₂₃H₃₂BrN₆O₅PSi
• Molecular Weight: 611.508

Synonyms:(S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate

Chemical Property of (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate

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Technology Process of (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate

There total 2 articles about (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate 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: 67.0%

8-bromo-2'-O-(tert-butyldimethylsilyl)adenosine-3',5'-cyclic phosphoric acid tri-n-butylammonium salt + benzylamine (100-46-9) → (SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate (872025-83-7)

Guidance literature:

8-bromo-2'-O-(tert-butyldimethylsilyl)adenosine-3',5'-cyclic phosphoric acid tri-n-butylammonium salt; With oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.5h;

benzylamine; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 2.16667h;

Reference yield: 49.0%

benzylamine (100-46-9) → (SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate (872025-83-7)

Guidance literature:

8-bromo-2'-O-(tert-butyldimethylsilyl)adenosine-3',5'-cyclic phosphoric acid tri-n-butylammonium salt; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at -65 ℃; for 1h;

benzylamine; In dichloromethane; at -65 - 20 ℃; for 3h;

Reference yield: 49.0%

(SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate (872025-83-7) + tributyl(4-fluorophenyl)stannane (17151-47-2) → (Rp)-8-(4-fluorophenyl)adenosine-2'O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate (872025-88-2)

Guidance literature:

palladium diacetate; triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 50 - 135 ℃; for 8h;

upstream raw materials:

benzylamine

Downstream raw materials:

(Rp)-8-(4-fluorophenyl)adenosine-2'O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoramidate

(Sp)-8-(2-thienyl)adenosine-2'O-(tert-butyldimethylsilyl)-3',5'-cyclic N-benzylphosphoroamidate

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