1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

Base Information

Chemical Name:1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine
CAS No.:160053-55-4
Molecular Formula:C₂₁H₂₆N₂O₈S
Molecular Weight:466.512
Hs Code.:

Synonyms:1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

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Chemical Property of 1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

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Technology Process of 1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

There total 5 articles about 1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>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: 83.0%

: 98-59-9
p-toluenesulfonyl chloride

: 160053-53-2
1-<1-deoxy-3,4-O-isopropylidene-β-D-psicofuranosyl>thymine

: 160053-55-4
1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

Guidance literature:: With dmap; triethylamine; In acetonitrile; at 0 ℃;
DOI:10.1080/15257779408013242

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 160053-55-4
1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / pyridine / 27 h / Ambient temperature

2: 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 30 min

3: 1.) BSA, 2.) TMSOTf / 1.) MeCN, room temperature, 1.5 h, 2.) 0 deg C, 1 h

4: 33 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

5: 83 percent / DMAP, Et₃N / acetonitrile / 0 °C

With benzenesulfonamide; dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; acetonitrile;
DOI:10.1080/15257779408013242

Reference yield:

: 130222-84-3
5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

: 160053-55-4
1-<3,4-O-isopropylidene-1-deoxy-6-O-(p-toluenesulfonyl)-β-D-psicofuranosyl>thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) THF, -78 deg C, 20 min, 2.) -78 deg C, 30 min

2: 1.) BSA, 2.) TMSOTf / 1.) MeCN, room temperature, 1.5 h, 2.) 0 deg C, 1 h

3: 33 percent / TBAF / tetrahydrofuran / 3 h / Ambient temperature

4: 83 percent / DMAP, Et₃N / acetonitrile / 0 °C

With benzenesulfonamide; dmap; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1080/15257779408013242