2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine

Base Information

• Chemical Name: 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine
• CAS No.: 1433368-95-6
• Molecular Formula: C₂₉H₃₄ClN₅O₃SeSi
• Molecular Weight: 643.119

Synonyms:2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine

Chemical Property of 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine

Chemical Property:

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Technology Process of 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine

There total 17 articles about 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine 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: 31.0%

(3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole (1006032-30-9) + 2-Amino-6-chloropurin (10310-21-1) → 7-[6-(tert-butyl-diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-6-chloro-7H-purin-2-ylamine (1433368-87-6) + 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine (1433368-95-6)

Guidance literature:

2-Amino-6-chloropurin; With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃;

(3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole; With 2,6-dimethylpyridine; iodosylbenzene; In 1,2-dichloro-ethane; at 85 ℃; for 8.5h;

DOI:10.1016/j.tet.2016.08.071

Reference yield: 25.0%

acetic acid 6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl ester (1006032-32-1) + 2-amino-6-chloropurine (10310-21-1) → 7-[6-(tert-butyl-diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-6-chloro-7H-purin-2-ylamine (1433368-87-6) + 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine (1433368-95-6)

Guidance literature:

2-amino-6-chloropurine; With N,O-bis-(trimethylsilyl)-acetamide; In toluene; at 95 ℃; for 1h; Inert atmosphere;

acetic acid 6-(tert-butyldiphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl ester; With trimethylsilyl trifluoromethanesulfonate; In toluene; at 95 ℃; for 15h; Inert atmosphere;

DOI:10.1002/chem.201300741

Reference yield:

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol (1006032-29-6) → 2-amino-6-chloro-9-(2,3-O-isopropylidene-5-O-tert-butyldiphenylsilyl-4-seleno-β-D-ribofuranosyl)-9H-purine (1433368-95-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; selenium / ethanol; tetrahydrofuran / 15 h / 60 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.75 h / -78 °C / Inert atmosphere

3.1: 1 h / 100 °C / Inert atmosphere

4.1: N,O-bis-(trimethylsilyl)-acetamide / toluene / 1 h / 95 °C / Inert atmosphere

4.2: 15 h / 95 °C / Inert atmosphere

With selenium; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1002/chem.201300741

upstream raw materials:

tert-butylchlorodiphenylsilane

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-L-lyxitol

5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1,4-di-O-methanesulfonyl-L-lyxitol

(3aS,4R,6aR)-tetrahydro-4-([(tert-butyl)dimethylsilyloxy]methyl)-2,2-dimethylselenopheno[3,4-d][1,3]dioxole

Downstream raw materials:

2-amino-9-[6-((tert-butyl)diphenylsilanyloxymethyl)-2,2-dimethyltetrahydro-1,3-dioxa-5-selenapentalen-4-yl]-1,9-dihydropurin-6-one

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