Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

Base Information

Chemical Name:Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester
CAS No.:894430-60-5
Molecular Formula:C₂₁H₂₂F₃N₃O₈S
Molecular Weight:533.482
Hs Code.:

Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

Synonyms:Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

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Chemical Property of Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

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Technology Process of Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

There total 2 articles about Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester 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:

: 1-[2-azido-3-O-benzyl-2-deoxy-5-O-methanesulfonyl-4-C-methanesulfonoxymethyl-L-erythro-pentofuranosyl]thymine

: 894430-60-5
Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 4.11 g / aq. NaOH; PMe₃ / tetrahydrofuran / 20 h / 20 °C

2: pyridine / 1.67 h / 20 °C

With pyridine; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; 1: Staudinger reaction;
DOI:10.1021/jo060331f

Reference yield:

: 894430-43-4
(1S,3R,4S,7R)-7-benzyloxy-1-methanesulfonoxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

: 407-25-0
trifluoroacetic anhydride

: 894430-60-5
Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

Guidance literature:: With pyridine; at 20 ℃; for 1.66667h;
DOI:10.1021/jo060331f

Reference yield:

: 894430-60-5
Methanesulfonic acid (1S,3R,4S,7R)-7-benzyloxy-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-1-ylmethyl ester

: 866611-96-3
(1S,3R,4S,7R)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 18-crown-6 / dioxane / 13 h / 80 °C

2: 7.12 g / NH₃ / methanol / 15 h / 20 °C

3: 83 percent / NaBH₄ / ethanol / 19 h / 20 °C

4: 73 percent / DMAP; pyridine / 2 h / 70 °C

5: 72 percent / ammonium formate / Pd(OH)2/C / ethyl acetate / 23 h / 65 °C

With pyridine; dmap; sodium tetrahydroborate; 18-crown-6 ether; ammonia; ammonium formate; palladium dihydroxide; In 1,4-dioxane; methanol; ethanol; ethyl acetate;
DOI:10.1021/jo060331f