4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

Base Information

Chemical Name:4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol
CAS No.:259137-70-7
Molecular Formula:C₂₆H₂₉ClN₄O₃Si
Molecular Weight:509.08
Hs Code.:

Synonyms:4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

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Chemical Property of 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

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Technology Process of 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

There total 7 articles about 4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol 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: 90.0%

: 122-51-0
orthoformic acid triethyl ester

: 259137-56-9
2(R)-(tert-butyldimethylsilyloxymethyl)-4(R)-(5-amino-6-chloro-4-pyrimidylamino)tetrahydrofuran-3(S)-ol

: 259137-70-7
4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

Guidance literature:: With hydrogenchloride; at 20 ℃; for 5h;
DOI:10.1080/07328319908044614

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 259137-70-7
4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 91 percent / H₂ / Pd/C / ethanol / 6 h / 1292.87 Torr

5: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C

6: 90 percent / conc. HCl / 5 h / 20 °C

With pyridine; hydrogenchloride; thionyl chloride; sodium azide; hydrogen; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; ethanol; N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Reduction / 5: Substitution / 6: Cyclization;
DOI:10.1080/07328319908044614

Reference yield:

: 491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9
1,4-anhydro-D-ribitol

: 259137-70-7
4(R)-(6-chloro-9H-purin-9-yl)-2(R)-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-3(S)-ol

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine / 0 °C

2: 1.04 g / SOCl₂; pyridine / 20 °C

3: 78 percent / NaN₃ / dimethylformamide / 3 h / 80 °C

4: 91 percent / H₂ / Pd/C / ethanol / 6 h / 1292.87 Torr

5: 52 percent / pyridine / 1-methyl-pyrrolidin-2-one / 5 h / 140 °C

6: 90 percent / conc. HCl / 5 h / 20 °C

With pyridine; hydrogenchloride; thionyl chloride; sodium azide; hydrogen; palladium on activated charcoal; In 1-methyl-pyrrolidin-2-one; ethanol; N,N-dimethyl-formamide; 1: Substitution / 2: Cyclization / 3: Ring cleavage / 4: Reduction / 5: Substitution / 6: Cyclization;
DOI:10.1080/07328319908044614