3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

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Chemical Name:3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
CAS No.:1269409-99-5
Molecular Formula:C₃₅H₄₇N₅O₈
Molecular Weight:665.787
Hs Code.:

Synonyms:3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

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Chemical Property of 3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

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Technology Process of 3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

There total 4 articles about 3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-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: 74.0%

: 1269409-98-4
3-[2'-deoxy-5'-O-[N-(fluorenylmethoxycarbonyl)valylprolylalanyl]-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

: 1269409-99-5
3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

Guidance literature:: With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;
DOI:10.1021/jm101624e

Reference yield:

: 109425-49-2
Fmoc-Val-Pro-OH

: 1269409-99-5
3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 15 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

3: di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 144 h / 20 °C / Inert atmosphere

4: piperidine / N,N-dimethyl-formamide / 0.08 h / 20 °C

With piperidine; di-tert-butyl-diazodicarboxylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Mitsunobu condensation;
DOI:10.1021/jm101624e

Reference yield:

: 1269409-88-2
Fmoc-Val-Pro-Ala-OtBu

: 1269409-99-5
3-[2'-deoxy-5'-O-(valylprolylalanyl)-β-D-ribofuranosyl]-6-(p-pentylphenyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

2: di-tert-butyl-diazodicarboxylate / tetrahydrofuran / 144 h / 20 °C / Inert atmosphere

3: piperidine / N,N-dimethyl-formamide / 0.08 h / 20 °C

With piperidine; di-tert-butyl-diazodicarboxylate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Mitsunobu condensation;
DOI:10.1021/jm101624e