9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

Base Information

Chemical Name:9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine
CAS No.:881915-63-5
Molecular Formula:C₄₂H₄₆ClFN₄O₂SSi₂
Molecular Weight:781.541
Hs Code.:

Synonyms:9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

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Chemical Property of 9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

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Technology Process of 9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

There total 8 articles about 9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine 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:

: (2R,3R)-2,3-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-thietane 1-oxide

: 1651-29-2
6-chloro-2-fluoropurine

: 881915-63-5
9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

: 9-[3,4-bis-(tert-butyl-diphenyl-silanyloxymethyl)-thietan-2-yl]-6-chloro-2-fluoro-9H-purine

Guidance literature:: 6-chloro-2-fluoropurine; With 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile; for 3h; Heating;

(2R,3R)-2,3-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-thietane 1-oxide; With trimethylsilyl trifluoromethanesulfonate; triethylamine; zinc(II) iodide; In toluene; at 0 ℃; for 24h;
DOI:10.1021/jm050912h

Reference yield:

: (2R,3S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-thietane-3-carbaldehyde

: 881915-63-5
9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOMe / methanol / 16 h

1.2: NaBH₄ / methanol / 2 h

2.1: 92 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

3.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

4.1: hexamethyldisilazane / acetonitrile / 3 h / Heating

4.2: Et₃N; TMSOTf; ZnI₂ / toluene / 24 h / 0 °C

With 1H-imidazole; sodium methylate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; dichloromethane; acetonitrile;
DOI:10.1021/jm050912h

Reference yield:

: 881915-51-1
(-)-(2R)-tert-butyl-(3-methylene-thietan-2-ylmethoxy)-diphenylsilane

: 881915-63-5
9-[(2R,3S,4S)-2,3-bis(tert-butyldiphenylsilanyloxymethyl)thietan-4-yl]-6-chloro-2-fluoropurine

Guidance literature:: Multi-step reaction with 6 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2.5 h / 0 - 20 °C

1.2: 64 percent / aq. H₂O₂; NaOH / tetrahydrofuran / 2 h

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: NaOMe / methanol / 16 h

3.2: NaBH₄ / methanol / 2 h

4.1: 92 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

5.1: mCPBA / CH₂Cl₂ / 0.5 h / -78 °C

6.1: hexamethyldisilazane / acetonitrile / 3 h / Heating

6.2: Et₃N; TMSOTf; ZnI₂ / toluene / 24 h / 0 °C

With 1H-imidazole; oxalyl dichloride; dimethylsulfide borane complex; sodium methylate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: Swern oxidation;
DOI:10.1021/jm050912h