1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

Base Information

Chemical Name:1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine
CAS No.:1182869-58-4
Molecular Formula:C₂₈H₄₆N₂O₇SSi₂
Molecular Weight:610.919
Hs Code.:

Synonyms:1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

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Chemical Property of 1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

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Technology Process of 1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

There total 9 articles about 1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]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: 92.0%

: 1182869-39-1
1-[4-benzenesulfonyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1182869-58-4
1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h;
DOI:10.1016/j.tet.2009.05.078

Reference yield:

: 131118-61-1
3'-tert-butyldimethylsilylthymidine 5'-carboxaldehyde

: 1182869-58-4
1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 24 h / 20 °C

2: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

4: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2009.05.078

Reference yield:

: 40733-27-5
3'-O-(t-butyldimethylsilyl)thymidine

: 1182869-58-4
1-[4-benzenesulfonyl-3,5-bis-O-(tert-butyldimethylsilyl)-2-deoxy-α-L-threo-pentofuranosyl]thymine

Guidance literature:: Multi-step reaction with 5 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 1 h / Reflux

2: triethylamine / dichloromethane / 24 h / 20 °C

3: sodium tetrahydroborate / methanol / 0.5 h / 20 °C

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 20 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 15 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2009.05.078