N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

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Chemical Name:N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
CAS No.:136010-42-9
Molecular Formula:C₂₅H₄₃N₃O₅S
Molecular Weight:497.7
Hs Code.:

Synonyms:N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

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Chemical Property of N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

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Technology Process of N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

There total 13 articles about N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane 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: 90.8%

: 122621-77-6
(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

: 119434-75-2,119378-93-7
(S)-3-(4-thiazolyl)-2-tert-butoxycarbonylaminopropanoic acid

: 136010-42-9
N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Guidance literature:: With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; 5 deg C, 5 min; rt, 18 h;
DOI:10.1080/00397919608004592

Reference yield:

: 139727-13-2
(4S,5R)-2,2-Dimethyl-4-(2-methyl-1-propenyl)-5-(hydroxymethyl)-1,3-dioxolane

: 136010-42-9
N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / H₂ / 10 percent Pd/C / methanol / 24 h / 760 Torr / Ambient temperature

3: 1.) t-BuLi / 1.) pentane, diethyl ether, -80 to -90 deg C, 5 min, 2.) ether, r.t., 1 h

4: 64 percent / H₂ / Raney nickel / methanol / 24 h / 3040 Torr / Ambient temperature

5: 6N HCl / methanol / 4 h / Ambient temperature

6: 1.) N-methylmorpholine, 1-hydroxybenzotriazole hydrate, 2.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1.) DMF, -23 deg C, 2.) r.t., 24 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; tert.-butyl lithium; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; nickel; In methanol;
DOI:10.1021/jo00064a013

Reference yield:

: 141364-53-6
N'-[(S)-2-Cyclohexyl-1-((4R,5S)-5-isobutyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-N,N-dimethyl-hydrazine

: 136010-42-9
N-(tert-butoxycarbonyl)-4-thiazolylalaninyl amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / H₂ / Raney nickel / methanol / 24 h / 3040 Torr / Ambient temperature

2: 6N HCl / methanol / 4 h / Ambient temperature

3: 1.) N-methylmorpholine, 1-hydroxybenzotriazole hydrate, 2.) 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / 1.) DMF, -23 deg C, 2.) r.t., 24 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; nickel; In methanol;
DOI:10.1021/jo00064a013