O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

Base Information

• Chemical Name: O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine
• CAS No.: 769141-96-0
• Molecular Formula: C₄₁H₅₄N₆O₅Si₂
• Molecular Weight: 767.088

Synonyms:O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

Chemical Property of O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

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Technology Process of O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

There total 3 articles about O⁶-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine 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: 62.0%

4-phenylalanine (92-67-1) + O6-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (328394-26-9) → O6-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (769141-96-0)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at 100 ℃; for 0.5h;

DOI:10.1021/ja0487022

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → O6-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (769141-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / 0 - 20 °C

2: 76 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

3: 62 percent / Pd₂(dba)3; BINAP; LiHMDS / toluene; tetrahydrofuran / 0.5 h / 100 °C

With pyridine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; toluene; 3: Buchwald-Hartwig reaction;

DOI:10.1021/ja0487022

Reference yield:

8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (769141-88-0) → O6-benzyl-8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine (769141-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

2: 62 percent / Pd₂(dba)3; BINAP; LiHMDS / toluene; tetrahydrofuran / 0.5 h / 100 °C

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; toluene; 2: Buchwald-Hartwig reaction;

DOI:10.1021/ja0487022

upstream raw materials:

4-phenylalanine

O⁶-benzyl-8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

8-bromo-2'-deoxyguanosine

8-bromo-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

Downstream raw materials:

8-[(1,1'-biphenyl)-4-ylamino]-N9-[3',5'-O-(1,1,3,3-tetrakis(isopropyl)-1,3-disiloxanediyl)-β-D-2'-deoxyribofuranosyl]guanine

N-(2′-deoxyguanosin-8-yl)-4-aminobiphenyl

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