1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

Base Information

Chemical Name:1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil
CAS No.:208463-25-6
Molecular Formula:C₃₄H₃₆N₂O₈S
Molecular Weight:632.734
Hs Code.:

Synonyms:1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

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Chemical Property of 1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

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Technology Process of 1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

There total 4 articles about 1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil 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: 89.0%

: 507-09-5
tiolacetic acid

: 208463-21-2
1-{(2R,3R,4R,5R)-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl}uracil

: 208463-25-6
1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/jo0003910

Reference yield:

: 134056-18-1
1-<(2R,3R,4R,5R)-3-<<3-(trifluoromethyl)benzoyl>oxy>-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil

: 208463-25-6
1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / triethylamine / tetrahydrofuran / 4 h / 20 °C

2: 96 percent / NaOH; water / methanol / 0.25 h

3: 89 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 3: Mitsunobu reaction;
DOI:10.1021/jo0003910

Reference yield:

: 134056-17-0
(1R,5R,6R,7R)-6-<(benzoyloxy)methyl>-7-<<3-(trifluoromethyl)benzoyl>oxy>-2,8-dioxabicyclo<3.2.1>octane

: 208463-25-6
1-{(2R,3R,4R,5R)-4-acetylthiomethyl-5-[2-(4,4'-dimethoxytriphenylmethoxy)ethyl]-3-hydroxytetrahydrofuran-2-yl}uracil

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile / 0.5 h / 20 °C

1.2: 96 percent / SnCl₄ / acetonitrile / 14 h / 20 °C

2.1: 95 percent / triethylamine / tetrahydrofuran / 4 h / 20 °C

3.1: 96 percent / NaOH; water / methanol / 0.25 h

4.1: 89 percent / diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 5 h / 20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; water; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; acetonitrile; 1.1: Vorbrueggen reaction / 4.1: Mitsunobu reaction;
DOI:10.1021/jo0003910