7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

Base Information

Chemical Name:7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol
CAS No.:146399-51-1
Molecular Formula:C₃₂H₅₁NO₅Si₂
Molecular Weight:585.932
Hs Code.:

Synonyms:7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

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Chemical Property of 7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

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Technology Process of 7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

There total 8 articles about 7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol 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: 75.0%

: 5,6-anhydro-2-azido-7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-D-glycero-L-allo-heptitol

: 146399-51-1
7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

Guidance literature:: With hydrogen; palladium; In ethanol; for 24h; Ambient temperature;
DOI:10.1016/S0040-4020(01)89046-3

Reference yield:

: 127903-44-0
2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptono-1,5-lactone

: 146399-51-1
7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

Guidance literature:: Multi-step reaction with 8 steps

1: iBu₂AlH / heptane; tetrahydrofuran / 1) -70 deg C, 1 h, 2) -20 deg C, 6 h

2: NaBH₄ / methanol / 1) 0 deg C, 1 h, 2) r.t., 1 h

3: 92 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

4: 90 percent / 4-N,N'-dimethylaminopyridine, pyridine / 12 h / Ambient temperature

5: 79 percent / 80percent aq. HOAc / dioxane / 1.5 h / 50 °C

6: 92 percent / Ba(OMe)2 / methanol / 0.5 h / Ambient temperature

7: 84 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

8: 75 percent / H₂ / Pd black / ethanol / 24 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen; diisobutylaluminium hydride; barium methoxide; acetic acid; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; n-heptane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89046-3

Reference yield:

: 2-azido-2-deoxy-3,4:6,7-di-O-isopropylidene-D-glycero-D-talo-heptose

: 146399-51-1
7-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-D-glycero-D-talo-heptitol

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄ / methanol / 1) 0 deg C, 1 h, 2) r.t., 1 h

2: 92 percent / imidazole / dimethylformamide / 5 h / Ambient temperature

3: 90 percent / 4-N,N'-dimethylaminopyridine, pyridine / 12 h / Ambient temperature

4: 79 percent / 80percent aq. HOAc / dioxane / 1.5 h / 50 °C

5: 92 percent / Ba(OMe)2 / methanol / 0.5 h / Ambient temperature

6: 84 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

7: 75 percent / H₂ / Pd black / ethanol / 24 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen; barium methoxide; acetic acid; palladium; In 1,4-dioxane; methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)89046-3