N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

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Chemical Name:N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide
CAS No.:753453-08-6
Molecular Formula:C₂₆H₃₇N₃O₆Si
Molecular Weight:515.682
Hs Code.:

Synonyms:N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

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Chemical Property of N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

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Technology Process of N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

There total 13 articles about N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-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: 94.0%

: 98-88-4
benzoyl chloride

: 162898-13-7
6-amino-3-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-5-methylpyrazin-2(1H)-one

: 753453-08-6
N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

Guidance literature:: With dmap; In pyridine; at 20 ℃; for 2h;
DOI:10.1002/hlca.200490120

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 753453-08-6
N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / -70 - -30 °C

2.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

2.2: 90 percent / CH₂Cl₂ / 0 - 20 °C

3.1: 92 percent / NH₃ / methanol / 74 h / 20 °C

4.1: 89 percent / H₂ / Pd/C / methanol / 48 h / 20 °C

5.1: 90 percent / AcOH / dioxane; H₂O / 1 h / 20 °C / pH 5

6.1: 99 percent / DMAP / pyridine / 0.5 h / 20 °C

7.1: 81 percent / LDA / tetrahydrofuran / 10 h / 20 °C

8.1: 94 percent / DMAP / pyridine / 2 h / 20 °C

With dmap; potassium tert-butylate; ammonia; hydrogen; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; 2.2: Wittig-Horner reaction / 5.1: Strecker-type condensation;
DOI:10.1002/hlca.200490120

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-Ribose

: 753453-08-6
N-{5-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-1,6-dihydro-3-methyl-6-oxo-pyrazin-2-yl}benzamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / H₂SO₄ / 1 h / 20 °C

2.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 6 h / -70 - -30 °C

3.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

3.2: 90 percent / CH₂Cl₂ / 0 - 20 °C

4.1: 92 percent / NH₃ / methanol / 74 h / 20 °C

5.1: 89 percent / H₂ / Pd/C / methanol / 48 h / 20 °C

6.1: 90 percent / AcOH / dioxane; H₂O / 1 h / 20 °C / pH 5

7.1: 99 percent / DMAP / pyridine / 0.5 h / 20 °C

8.1: 81 percent / LDA / tetrahydrofuran / 10 h / 20 °C

9.1: 94 percent / DMAP / pyridine / 2 h / 20 °C

With dmap; sulfuric acid; potassium tert-butylate; ammonia; hydrogen; acetic acid; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; 3.2: Wittig-Horner reaction / 6.1: Strecker-type condensation;
DOI:10.1002/hlca.200490120