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

Base Information

• Chemical Name: (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate
• CAS No.: 872025-03-1
• Molecular Formula: C₂₂H₃₀BrN₆O₅PSi
• Molecular Weight: 597.481

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

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

Chemical Property:

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

There total 2 articles about (S_P)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate 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: 68.0%

8-bromo-2'-O-(tert-butyldimethylsilyl)adenosine-3',5'-cyclic phosphoric acid tri-n-butylammonium salt + aniline (62-53-3) → (SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate (872025-03-1)

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 -20 - 20 ℃;

aniline; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1039/b702403g

Reference yield:

C16H24ClBrN5PO5Si + aniline (62-53-3) → (SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate (872025-03-1)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 3h; Product distribution / selectivity;

Reference yield: 92.0%

(SP)-8-bromoadenosine-2'-O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate (872025-03-1) + tributyl(furan-3-yl)stannane (87453-06-3) → (Sp)-8-(3-furyl)-adenosine-2'O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate (872025-09-7)

Guidance literature:

palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 50 - 85 ℃; for 2.5h;

upstream raw materials:

aniline

Downstream raw materials:

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

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

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

(Sp)-8-phenyladenosine-2'O-(tert-butyldimethylsilyl)-3',5'-cyclic N-phenylphosphoramidate

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