(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

Base Information

Chemical Name:(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate
CAS No.:252719-85-0
Molecular Formula:C₂₅H₃₀N₁₀O₆
Molecular Weight:566.577
Hs Code.:

(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

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Chemical Property of (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

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Technology Process of (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

There total 11 articles about (2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate 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:

: 3182-95-4
L-Phenylalaninol

: 252719-85-0
(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / 2-methoxy-ethanol / Heating

2: 68 percent / 4-(dimethylamino)pyridine; Et₃N / dimethylformamide / 20 °C

3: POCl₃; tetraethylammonium chloride; N,N-dimethylaniline / acetonitrile / 1.17 h / Heating

4: 9.4 g / MeOH; K₂CO₃ / 20 °C

5: 85 percent / ammonia / methanol / 24 h / 90 - 100 °C

6: N,O-bis(trimethylsilyl)acetamide / trimethylsilyl trifluoromethanesulfonate / acetonitrile / Heating

With methanol; dmap; N,O-bis-(trimethylsilyl)-acetamide; tetraethylammonium chloride; ammonia; potassium carbonate; N,N-dimethyl-aniline; triethylamine; trichlorophosphate; trimethylsilyl trifluoromethanesulfonate; In methanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo049963x

Reference yield:

: 87781-93-9
2-bromo-6-hydroxypurine

: 252719-85-0
(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / 2-methoxy-ethanol / Heating

2: 68 percent / 4-(dimethylamino)pyridine; Et₃N / dimethylformamide / 20 °C

3: POCl₃; tetraethylammonium chloride; N,N-dimethylaniline / acetonitrile / 1.17 h / Heating

4: 9.4 g / MeOH; K₂CO₃ / 20 °C

5: 85 percent / ammonia / methanol / 24 h / 90 - 100 °C

6: N,O-bis(trimethylsilyl)acetamide / trimethylsilyl trifluoromethanesulfonate / acetonitrile / Heating

With methanol; dmap; N,O-bis-(trimethylsilyl)-acetamide; tetraethylammonium chloride; ammonia; potassium carbonate; N,N-dimethyl-aniline; triethylamine; trichlorophosphate; trimethylsilyl trifluoromethanesulfonate; In methanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo049963x

Reference yield:

: (2R,3S,4R,5R)-2-(2-Ethyl-2H-tetrazol-5-yl)-5-methoxy-tetrahydro-furan-3,4-diol

: 252719-85-0
(2R,3R,4R,5R)-2-(6-amino-2-{[(1S)-2-hydroxy-1-(phenylmethyl)ethyl]amino}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydrofuran-3,4-diyl diacetate

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine / ethyl acetate / 5 - 20 °C

2: H₂SO₄ / ethyl acetate / 4 h / 60 - 65 °C

3: N,O-bis(trimethylsilyl)acetamide / trimethylsilyl trifluoromethanesulfonate / acetonitrile / Heating

With pyridine; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; trimethylsilyl trifluoromethanesulfonate; In ethyl acetate; acetonitrile;
DOI:10.1021/jo049963x