1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

Base Information

Chemical Name:1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine
CAS No.:921202-86-0
Molecular Formula:C₂₄H₂₀F₂N₂O₆S
Molecular Weight:502.495
Hs Code.:

Synonyms:1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

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Chemical Property of 1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

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Technology Process of 1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

There total 10 articles about 1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine 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: 73.0%

: 921202-77-9
1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose

: 65-71-4,28806-14-6,691841-57-3
thymin

: 921202-86-0
1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

Guidance literature:: 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose; thymin; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 0.5h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 0 - 80 ℃;
DOI:10.1021/ol062576k

Reference yield:

: Benzoic acid (2R,4R)-4-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-difluoro-2-trifluoromethanesulfonyloxy-butyl ester

: 921202-86-0
1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / CsF / dimethylformamide / 13 h / 20 °C

2.1: CF₃COOH / tetrahydrofuran; H₂O / 1 h

2.2: NaIO₄ / methanol; H₂O / 1.5 h

2.3: 64 percent / HCl / methanol

3.1: 97 percent / DMAP / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 87 percent / NaBrO₃ / ethyl acetate; H₂O / 0.33 h / 20 °C

5.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 0.33 h / 20 °C

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

6.2: 73 percent / TMSOTf / acetonitrile / 0 - 80 °C

With dmap; sodium bromate; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; cesium fluoride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 6.1: Vorbrueggen glycosylation;
DOI:10.1021/ol062576k

Reference yield:

: 921202-72-4
1-O-acetyl-5-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranose

: 921202-86-0
1-(2,5-di-O-benzoyl-3-deoxy-3,3-difluoro-4-thio-β-L-xylofuranosyl)thymine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 0.33 h / 20 °C

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

2.2: 73 percent / TMSOTf / acetonitrile / 0 - 80 °C

With dmap; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; In dichloromethane; acetonitrile; 2.1: Vorbrueggen glycosylation;
DOI:10.1021/ol062576k