(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Base Information

Chemical Name:(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine
CAS No.:1365993-63-0
Molecular Formula:C₂₃H₃₃N₅O₃S
Molecular Weight:459.613
Hs Code.:

Synonyms:(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

There total 11 articles about (2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine 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:

: 1365993-56-1
methyl (S,E)-3-[N-allyl-N-(tert-butoxycarbonyl)amino]hept-5-enoate

: 1365993-63-0
(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: Grubbs catalyst first generation / dichloromethane / 12 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 12 h / 50 °C

2.2: pH 4

3.1: iodine; sodium hydrogencarbonate / acetonitrile / 12 h / -20 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.58 h / -78 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere

5.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

6.2: 16 h / 0 - 20 °C / Inert atmosphere

7.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr

8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With Grubbs catalyst first generation; lithium hydroxide monohydrate; 20 % Pd(OH)2/C; hydrogen; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 6.1: Wittig reaction / 6.2: Wittig reaction / 8.1: Mitsunobu reaction;
DOI:10.1021/ol300209s

Reference yield:

: 1365993-58-3
(S,S,S)-N⁽⁶⁾-tert-butoxycarbonyl-8-iodo-2-oxa-6-azabicyclo[3.3.1]nonan-3-one

: 1365993-63-0
(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.58 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

3.2: 16 h / 0 - 20 °C / Inert atmosphere

4.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr

5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With 20 % Pd(OH)2/C; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 3.1: Wittig reaction / 3.2: Wittig reaction / 5.1: Mitsunobu reaction;
DOI:10.1021/ol300209s

Reference yield:

: 1365993-57-2
(S)-2-[1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-2-yl]ethanoic acid

: 1365993-63-0
(2R,4S,5R)-1-tert-butoxycarbonyl-2-(6-[1-phenyl-1H-tetrazol-5-ylsulfanyl]hexyl)-4,5-epoxypiperidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: iodine; sodium hydrogencarbonate / acetonitrile / 12 h / -20 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.58 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere

3.1: sodium hydroxide / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere

4.2: 16 h / 0 - 20 °C / Inert atmosphere

5.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 2 h / 20 °C / 760.05 Torr

6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

With 20 % Pd(OH)2/C; hydrogen; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 4.1: Wittig reaction / 4.2: Wittig reaction / 6.1: Mitsunobu reaction;
DOI:10.1021/ol300209s