1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone

Base Information

• Chemical Name: 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone
• CAS No.: 137410-66-3
• Molecular Formula: C₂₄H₃₂N₂O₆Si
• Molecular Weight: 472.613

Synonyms:1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone

Chemical Property of 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone

Chemical Property:

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Technology Process of 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone

There total 3 articles about 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone 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: 35.0%

1-<5'-O-(tert-Butyldimethylsilyl)-2'-O-cinnamoyl-3'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil (163254-10-2) → 1-<5'-O-(tert-Butyldimethylsilyl)-2'-O-cinnamoyl-3'-deoxy-β-D-ribofuranosyl>uracil + 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone (137410-66-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 20h; Heating;

DOI:10.1021/jo00104a021

Reference yield:

Cinnamoyl chloride (102-92-1,17082-09-6) → 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone (137410-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridine / 1.) CH₂Cl₂, r.t., 3 h, 2.) DMF, r.t., overnight

2: 35 percent / Bu₃SnH, AIBN / benzene / 20 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1021/jo00104a021

Reference yield:

5'-O-(tert-butyldimethylsilyl)uridine (87418-77-7,54925-65-4) → 1-<5'-O-(tert-Butyldimethylsilyl)-3'-C-<(S)carboxybenzylmethyl>-3'-deoxy-β-D-ribofuranosyl>uracil 2',3'-γ-lactone (137410-66-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) pyridine / 1.) CH₂Cl₂, r.t., 3 h, 2.) DMF, r.t., overnight

2: 35 percent / Bu₃SnH, AIBN / benzene / 20 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1021/jo00104a021

upstream raw materials:

1-<5'-O-(tert-Butyldimethylsilyl)-2'-O-cinnamoyl-3'-O-<(imidazol-1-yl)thiocarbonyl>-β-D-ribofuranosyl>uracil

Cinnamoyl chloride

5'-O-(tert-butyldimethylsilyl)uridine

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