(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

Base Information

Chemical Name:(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one
CAS No.:152005-88-4
Molecular Formula:C₂₇H₃₇NO₅Si
Molecular Weight:483.68
Hs Code.:

Synonyms:(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

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Chemical Property of (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

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Technology Process of (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

There total 10 articles about (5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one 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:

: (3aS,9S,9aS,9bR)-9-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-hexahydro-1,3,5-trioxa-5a-aza-cyclopenta[a]naphthalen-6-one

: 152005-88-4
(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In ethanol; at 0 ℃; for 1h;
DOI:10.1021/jo00074a040

Reference yield:

: 75629-74-2
(S)-(-)-Tetrahydro-5-oxo-2-furancarboxaldehyde

: 152005-88-4
(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

2: 94 percent / potassium tert-butoxide / tetrahydrofuran / 0.25 h / Ambient temperature

3: tetrahydrofuran; methanol; H₂O / 0.5 h / Ambient temperature

4: imidazole, 4-DMAP / dimethylformamide / 72 h / Ambient temperature

5: 94 percent / LiOH*H₂O / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

6: 100 percent / pyridine / tetrahydrofuran / Ambient temperature

7: 80 percent / diisopropylamine, NH₂OH*HCl / CHCl₃ / 1.) 0 deg C, 30 min, 2.) 0 deg C, 2 h

8: (n-Pr)4NIO₄ / CH₂Cl₂ / 1.) -78 deg C, 4 h, 2.) -78 to 0 deg C, 30 min

9: 1.) NMO, OsO₄, 2.) Dowex H⁽¹⁺⁾ resin / 1.) acetone, water, THF, room temp., 24 h, 2.) room temp., 4 h

10: Na₂HPO₄, 6percent Na(Hg) / ethanol / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; disodium hydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; tetrapropylammonium periodate; Dowex H⁽¹⁺⁾ resin; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; potassium tert-butylate; diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00074a040

Reference yield:

: 151915-16-1
(S)-(+)-Dihydro-5-<(E)-1,3-butadienyl>-2(3H)-furanone

: 152005-88-4
(5S,6S)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-piperidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran; methanol; H₂O / 0.5 h / Ambient temperature

2: imidazole, 4-DMAP / dimethylformamide / 72 h / Ambient temperature

3: 94 percent / LiOH*H₂O / tetrahydrofuran; methanol / 0.25 h / Ambient temperature

4: 100 percent / pyridine / tetrahydrofuran / Ambient temperature

5: 80 percent / diisopropylamine, NH₂OH*HCl / CHCl₃ / 1.) 0 deg C, 30 min, 2.) 0 deg C, 2 h

6: (n-Pr)4NIO₄ / CH₂Cl₂ / 1.) -78 deg C, 4 h, 2.) -78 to 0 deg C, 30 min

7: 1.) NMO, OsO₄, 2.) Dowex H⁽¹⁺⁾ resin / 1.) acetone, water, THF, room temp., 24 h, 2.) room temp., 4 h

8: Na₂HPO₄, 6percent Na(Hg) / ethanol / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; disodium hydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; tetrapropylammonium periodate; Dowex H⁽¹⁺⁾ resin; hydroxylamine hydrochloride; diisopropylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00074a040