(2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine

Base Information

• Chemical Name: (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine
• CAS No.: 402757-26-0
• Molecular Formula: C₂₃H₃₀F₃N₃O₃SSi
• Molecular Weight: 513.656

Synonyms:(2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine

Chemical Property of (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine

Chemical Property:

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Technology Process of (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine

There total 10 articles about (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 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:

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate (402757-16-8) → (2'R)-L-N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine (402757-26-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: H₂ / 10percent Pd/C / ethanol / 24 h / 20 °C / 760.05 Torr

2.1: 3.8 g / 1 N HCl / 24 h / 50 - 55 °C / 60 Torr

3.1: 37 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

4.1: 87 percent / NaBH₄ / methanol / 1.5 h / 0 °C

5.1: pyridine / 12 h / 0 - 20 °C

6.1: 491 mg / Na₂S*9H₂O / dimethylformamide / 4 h / 100 °C

7.1: m-CPBA / CH₂Cl₂ / 3 h / -78 °C

8.1: 222 mg / 4.5 h / 100 °C

9.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

9.2: 172 mg / trimethylsilyl triflate / acetonitrile / 24 h / 0 - 20 °C

With 1H-imidazole; hydrogenchloride; sodium sulfide; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; hydrogen; 3-chloro-benzenecarboperoxoic acid; 10percent Pd/C; In pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 8.1: Pummerer reaction;

DOI:10.1021/jo0159690

Reference yield:

4-N-benzoylcytosine (26661-13-2) + (3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate (402757-22-6) → (2'R)-L-N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine (402757-26-0) + (2'R)-L-N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine (402757-24-8)

Guidance literature:

4-N-benzoylcytosine; (3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 0.5h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 20 ℃; for 24h; Further stages.;

DOI:10.1021/jo0159690

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2'R)-L-N4-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine (402757-26-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 37 percent / imidazole / CH₂Cl₂ / 0.83 h / 20 °C

2.1: 87 percent / NaBH₄ / methanol / 1.5 h / 0 °C

3.1: pyridine / 12 h / 0 - 20 °C

4.1: 491 mg / Na₂S*9H₂O / dimethylformamide / 4 h / 100 °C

5.1: m-CPBA / CH₂Cl₂ / 3 h / -78 °C

6.1: 222 mg / 4.5 h / 100 °C

7.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 0.5 h / Heating

7.2: 172 mg / trimethylsilyl triflate / acetonitrile / 24 h / 0 - 20 °C

With 1H-imidazole; sodium sulfide; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; 3-chloro-benzenecarboperoxoic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6.1: Pummerer reaction;

DOI:10.1021/jo0159690

upstream raw materials:

4-N-benzoylcytosine

(3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate

tert-butyldimethylsilyl chloride

(Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate

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