2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

Base Information

Chemical Name:2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide
CAS No.:753453-01-9
Molecular Formula:C₂₄H₃₆N₄O₇SSi
Molecular Weight:552.724
Hs Code.:

Synonyms:2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

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Chemical Property of 2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

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Technology Process of 2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

There total 8 articles about 2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide 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: 72.0%

: 7669-54-7
2-nitrobenzenesulfenyl chloride

: 753453-00-8
2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)glycinamide

: 753453-01-9
2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

Guidance literature:: With 1,2,2,6,6-pentamethylpiperidine; In tetrahydrofuran; at 90 ℃; for 5.5h;
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

: 753453-01-9
2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

Guidance literature:: Multi-step reaction with 6 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: 93 percent / AcOH / dioxane; H₂O / 2 h / 20 °C / pH 6

6.1: 72 percent / 1,2,2,6,6-pentamethylpiperidine / tetrahydrofuran / 5.5 h / 90 °C

With 1,2,2,6,6-pentamethylpiperidine; dmap; potassium tert-butylate; ammonia; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 2.2: Wittig-Horner reaction;
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

: 753453-01-9
2-{5-O-[(tert-butyl)dimethylsilyl]-2,3-O-isopropylidene-β-D-ribofuranosyl}-N-(cyanomethyl)-N-[(2-nitrophenyl)thio]glycinamide

Guidance literature:: Multi-step reaction with 7 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: 93 percent / AcOH / dioxane; H₂O / 2 h / 20 °C / pH 6

7.1: 72 percent / 1,2,2,6,6-pentamethylpiperidine / tetrahydrofuran / 5.5 h / 90 °C

With 1,2,2,6,6-pentamethylpiperidine; dmap; sulfuric acid; potassium tert-butylate; ammonia; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 3.2: Wittig-Horner reaction;
DOI:10.1002/hlca.200490120