4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

Base Information

Chemical Name:4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine
CAS No.:384334-56-9
Molecular Formula:C₁₉H₁₉N₅O₄
Molecular Weight:381.391
Hs Code.:

Synonyms:4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

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Chemical Property of 4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

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Technology Process of 4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

There total 6 articles about 4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine 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: 93.0%

: 743476-64-4
4-amino-7-[3-(benzylamino)-5-O-(tert-butyldiphenylsilyl)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

: 384334-56-9
4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jo010935d

Reference yield:

: 69-33-0
tubercidin

: 384334-56-9
4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: α-acetoxyisobutyryl chloride / H2O; acetonitrile / 0.75 h / 20 °C

1.2: 100 percent / Dowex 1 x 2 (OH^-) / methanol / 2 h / 20 °C

2.1: 90 percent / pyridine / 12 h / 20 °C

3.1: 84 percent / Me₂BBr; Et₃N / CH₂Cl₂ / -78 - -15 °C

4.1: 84 percent / Et₃N / tetrahydrofuran; acetonitrile / 48 h / 20 °C

5.1: 97 percent / NaH / tetrahydrofuran / 12 h / -20 °C

6.1: 93 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With dimethylboron bromide; tetrabutyl ammonium fluoride; sodium hydride; 2-acetoxy-2-methylpropanoyl chloride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;
DOI:10.1021/jo010935d

Reference yield:

: 40627-31-4
4-amino-7-(2,3-anhydro-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

: 384334-56-9
4-amino-7-[3-(benzylamino)-3-N,2-O-carbonyl-3-deoxy-β-D-ribofuranosyl]pyrrolo[2,3-d]pyrimidine

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / pyridine / 12 h / 20 °C

2: 84 percent / Me₂BBr; Et₃N / CH₂Cl₂ / -78 - -15 °C

3: 84 percent / Et₃N / tetrahydrofuran; acetonitrile / 48 h / 20 °C

4: 97 percent / NaH / tetrahydrofuran / 12 h / -20 °C

5: 93 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With dimethylboron bromide; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
DOI:10.1021/jo010935d