3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one

Base Information

• Chemical Name: 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one
• CAS No.: 1065269-51-3
• Molecular Formula: C₂₄H₃₃N₅O₃Si
• Molecular Weight: 467.643

Synonyms:3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one

Chemical Property of 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one

Chemical Property:

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Technology Process of 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one

There total 2 articles about 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one 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: 84.0%

(E)-3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylprop-2-en-1-one (1065269-49-9) → 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one (1065269-51-3)

Guidance literature:

With phenylsilane; indium(III) acetate; In ethanol; at 20 ℃;

DOI:10.1016/j.bmcl.2008.07.015

Reference yield: 71.0%

3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide (1065269-52-4) → 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one (1065269-51-3)

Guidance literature:

With phenylmagnesium bromide; In tetrahydrofuran; at -78 ℃; for 5h; Cooling with ice;

DOI:10.1016/j.bmcl.2008.07.015

Reference yield: 92.0%

3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylpropan-1-one (1065269-51-3) → 3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxytetrahydrofuran-2-yl]-1-phenylpropan-1-one (1065269-46-6)

Guidance literature:

With hydrogen fluoride; triethylamine; In tetrahydrofuran; at 20 ℃; for 30h;

DOI:10.1016/j.bmcl.2008.07.015

upstream raw materials:

(E)-3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-1-phenylprop-2-en-1-one

3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-yl]-N-methoxy-N-methylpropanamide

Downstream raw materials:

3-[(2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxytetrahydrofuran-2-yl]-1-phenylpropan-1-one

3-[(2R,3S,5R)-3-(tert-butyldimethylsilyloxy)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-2-yl]-1-phenylpropan-1-one

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