(+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine

Base Information

• Chemical Name: (+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine
• CAS No.: 875484-21-2
• Molecular Formula: C₂₉H₄₇N₃O₄SSi₂
• Molecular Weight: 589.947

Synonyms:(+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine

Chemical Property of (+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine

There total 7 articles about (+/-)-N⁴-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine 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: 66.0%

(+/-)-acetic acid 4,4-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl ester (875484-18-7) + 4-N-benzoylcytosine (26661-13-2) → (+/-)-N4-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine (875484-21-2)

Guidance literature:

4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Heating;

(+/-)-acetic acid 4,4-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl ester; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1002/ardp.200500174

Reference yield:

3,3-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophene (875484-17-6) → (+/-)-N4-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine (875484-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: m-CPBA / CH₂Cl₂ / 1 h / -78 °C

2.1: 871 mg / 2 h / 110 °C

3.1: HMDS; ammonium sulfate / Heating

3.2: 66 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 °C

With ammonium sulfate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; 2.1: Pummerer rearrangement / 3.1: Vorbrueggen glycosyl condensation;

DOI:10.1002/ardp.200500174

Reference yield:

2,2-bis(tert-butyldimethylsilanyloxymethyl)butane-1,4-diol (875484-15-4) → (+/-)-N4-benzoyl-1-[3,3-C-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl]cytosine (875484-21-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2.1: 60 percent / Na₂S / dimethylformamide / 0 °C

3.1: m-CPBA / CH₂Cl₂ / 1 h / -78 °C

4.1: 871 mg / 2 h / 110 °C

5.1: HMDS; ammonium sulfate / Heating

5.2: 66 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 20 °C

With sodium sulfide; ammonium sulfate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; N,N-dimethyl-formamide; 4.1: Pummerer rearrangement / 5.1: Vorbrueggen glycosyl condensation;

DOI:10.1002/ardp.200500174

upstream raw materials:

(+/-)-acetic acid 4,4-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophen-2-yl ester

4-N-benzoylcytosine

3,3-bis(tert-butyldimethylsilanyloxymethyl)tetrahydrothiophene

2,2-bis(tert-butyldimethylsilanyloxymethyl)butane-1,4-diol

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