N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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Chemical Name:N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
CAS No.:176747-33-4
Molecular Formula:C₂₂H₂₉N₃O₆S₂
Molecular Weight:495.621
Hs Code.:

Synonyms:N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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Chemical Property of N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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Technology Process of N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

There total 7 articles about N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 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: 74.0%

: 84592-34-7
1-t-butylthiohydrazine-1,2-dicarboxmorpholide

: 176747-32-3
Thiobenzoic acid S-{2-[(2R,3R,4R,5R)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-3-yloxy]-ethyl} ester

: 176747-33-4
N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 0 ℃; for 0.75h;
DOI:10.1021/ja960091t

Reference yield:

: N-[1-((2R,3R,3aR,9aR)-3-Allyloxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

: 176747-33-4
N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / N-methylmorpholine N-oxide, aq. OsO₄ / acetone / 2.5 h / Ambient temperature

2: 97 percent / aq. NaIO₄ / dioxane / 4.5 h / Ambient temperature

3: 93 percent / NaBH₄ / methanol / 90 h / Ambient temperature

4: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

5: 76 percent / Et₃N / dimethylformamide / Ambient temperature

6: 100 percent / 48percent aq. HF / acetonitrile / 7 h / Ambient temperature

7: 74 percent / LiOH*H₂O / methanol; tetrahydrofuran / 0.75 h / 0 °C

With pyridine; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; hydrogen fluoride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja960091t

Reference yield:

: 176747-28-7
N-{2-Oxo-1-[(2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-(2-oxo-ethoxy)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-1,2-dihydro-pyrimidin-4-yl}-benzamide

: 176747-33-4
N-{1-[(2R,3R,4R,5R)-3-(2-tert-Butyldisulfanyl-ethoxy)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / NaBH₄ / methanol / 90 h / Ambient temperature

2: 92 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3: 76 percent / Et₃N / dimethylformamide / Ambient temperature

4: 100 percent / 48percent aq. HF / acetonitrile / 7 h / Ambient temperature

5: 74 percent / LiOH*H₂O / methanol; tetrahydrofuran / 0.75 h / 0 °C

With pyridine; lithium hydroxide; sodium tetrahydroborate; hydrogen fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja960091t