N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanine

Base Information

• Chemical Name: N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanine
• CAS No.: 1370348-34-7
• Molecular Formula: C₄₀H₃₇N₇O₅
• Molecular Weight: 695.778

Synonyms:N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanine

Chemical Property of N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanine

Chemical Property:

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Technology Process of N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanine

There total 8 articles about N⁹-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)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:

N9-[(2R,6S)-6-{(tert-butyldimethylsilyloxy)methyl}-4-tritylmorpholin-2-yl]-N2-(phenoxyacetyl)-O6-(2-cyanoethyl)guanine (1370348-33-6) → N9-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N2-(phenoxyacetyl)-O6-(2-cyanoethyl)guanine (1370348-34-7)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In dichloromethane; at 20 ℃; for 17h;

Reference yield:

Phenoxyacetyl chloride (701-99-5) → N9-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N2-(phenoxyacetyl)-O6-(2-cyanoethyl)guanine (1370348-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: chloro-trimethyl-silane; pyridine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / Cooling with ice

2.1: hydrogenchloride; sodium periodate / methanol; water / 3 h / 20 °C / Cooling with ice

2.2: 0.33 h / Cooling with ice

2.3: 4 °C

3.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

4.1: 1H-imidazole / dichloromethane / 1 h / 20 °C

5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

6.1: 1-Methylpyrrolidine / dichloromethane / 1 h / Cooling with ice

6.2: 2 h / Cooling with ice

7.1: triethylamine tris(hydrogen fluoride) / dichloromethane / 17 h / 20 °C

With 1-Methylpyrrolidine; pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium periodate; chloro-trimethyl-silane; triethylamine tris(hydrogen fluoride); triethylamine; In methanol; dichloromethane; water;

Reference yield:

N9-[(2R,6S)-6-{(tert-butyldimethylsilyloxy)methyl}-4-tritylmorpholin-2-yl]-N2-(phenoxacetyl)guanine (1370348-31-4) → N9-[(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2-yl]-N2-(phenoxyacetyl)-O6-(2-cyanoethyl)guanine (1370348-34-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice

2.1: 1-Methylpyrrolidine / dichloromethane / 1 h / Cooling with ice

2.2: 2 h / Cooling with ice

3.1: triethylamine tris(hydrogen fluoride) / dichloromethane / 17 h / 20 °C

With 1-Methylpyrrolidine; dmap; triethylamine tris(hydrogen fluoride); triethylamine; In dichloromethane;

upstream raw materials:

N²-(phenoxyacetyl)guanosine

N⁹-{(2R,6S)-6-(hydroxymethyl)morpholin-2-yl}-N²-(phenoxyacetyl)guanine p-toluenesulfonate

N⁹-{(2R,6S)-6-hydroxymethyl-4-tritylmorpholin-2yl}-N²-(phenoxyacetyl)guanine

N⁹-[(2R,6S)-6-{(tert-butyldimethylsilyloxy)methyl}-4-tritylmorpholin-2-yl]-N²-(phenoxacetyl)guanine

Downstream raw materials:

[(2S,6R)-6-{N²-(phenoxyacetyl)-O⁶-(2-cyanoethyl)guanin-9-yl}-4-tritylmorpholin-2-yl]methyl dimethylphosphoramidochloridate

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