1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

Base Information

Chemical Name:1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine
CAS No.:191163-58-3
Molecular Formula:C₂₈H₃₂N₂O₈S
Molecular Weight:556.637
Hs Code.:

Synonyms:1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

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Chemical Property of 1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

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Technology Process of 1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

There total 13 articles about 1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)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%

: 124-63-0
methanesulfonyl chloride

: 191163-49-2
1-(3-C-allyl-3,5-di-O-benzyl-β-D-ribo-pentofuranosyl)thymine

: 191163-58-3
1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

Guidance literature:: With pyridine;
DOI:10.1080/07328319708006201

Reference yield:

: 100-39-0
benzyl bromide

: 191163-58-3
1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

2: aq. AcOH / 3 h / 90 °C

3: pyridine / 48 h / Ambient temperature

4: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

5: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

6: 89 percent / pyridine / 1 h / Ambient temperature

With pyridine; benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; In methanol; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 191163-58-3
1-(3-C-Allyl-3,5-di-O-benzyl-2-O-methylsulfonyl-β-D-ribofuranosyl)thymine

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran; diethyl ether / 2 h / 0 °C

2: TBAF / tetrahydrofuran / 1 h / Ambient temperature

3: 86 percent / NaH / dimethylformamide / 1.) 50 deg C, 1 h, 2.) r.t., 18 h

4: aq. AcOH / 3 h / 90 °C

5: pyridine / 48 h / Ambient temperature

6: 86 percent / BSA, TMS triflate / acetonitrile / 1.) reflux, 1 h, 2.) r.t., 12 h

7: 95 percent / CH₃ONa / methanol / 16 h / Ambient temperature

8: 89 percent / pyridine / 1 h / Ambient temperature

With pyridine; benzenesulfonamide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile;