2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine

Base Information

• Chemical Name: 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine
• CAS No.: 115945-77-2
• Molecular Formula: C₃₁H₃₄N₄O₆
• Molecular Weight: 558.634

Synonyms:2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine

Chemical Property of 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine

Chemical Property:

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Technology Process of 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine

There total 2 articles about 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-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: 54.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 2-amino-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine (115945-74-9) → 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine (115945-77-2)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; Ambient temperature; liquid-liquid phase-transfer glycosylation;

DOI:10.1039/P19880000697

Reference yield:

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine (115945-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / 1M-sodium isobutoxide / 3 h / Heating

2: 54 percent / 50percent aq. NaOH / Bu₄NHSO₄ / CH₂Cl₂ / Ambient temperature; liquid-liquid phase-transfer glycosylation

With sodium hydroxide; sodium isobutoxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane;

DOI:10.1039/P19880000697

Reference yield:

2-amino-7-<2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl>-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine (115945-77-2) → 7-deaza-2'-deoxyguanosine (86392-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 1.0M sodium methoxide / methanol / 12 h / Ambient temperature

2: 86 percent / 2M aq. NaOH / 4 h / Heating

With sodium hydroxide; sodium methylate; In methanol;

DOI:10.1039/P19880000697

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

2-amino-4-isobutoxy-7H-pyrrolo<2,3-d>pyrimidine

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Downstream raw materials:

7-deaza-2'-deoxyguanosine

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