phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

Base Information

Chemical Name:phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate
CAS No.:134848-87-6
Molecular Formula:C₃₀H₄₇N₅O₇
Molecular Weight:589.732
Hs Code.:

Synonyms:phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

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Chemical Property of phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

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Technology Process of phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

There total 9 articles about phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate 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:

: 13574-13-5
Boc-Glu(OBzl)-OH

: (2S,3R,4S)-2-Amino-7-azido-1-cyclohexyl-heptane-3,4-diol

: 134848-87-6
phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; Yield given;
DOI:10.1021/jm00113a005

Reference yield:

: (2S,3R)-2-Amino-7-azido-1-cyclohexyl-3-hydroxy-heptan-4-one

: 134848-87-6
phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

2: 44 percent / NaBH₄ / methanol / 0.25 h / 0 °C

3: TFA / CH₂Cl₂ / Ambient temperature

4: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

With sodium tetrahydroborate; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jm00113a005

Reference yield:

: 134848-81-0
(4S,5R)-4-(cyclohexylmethyl)-5-<2-(3-hydroxypropyl)-1,3-dioxolan-2-yl>-2-oxazolidinone

: 134848-87-6
phenylmethyl (4S)-5-<(2S,3R,4S)-7-azido-1-cyclohexyl-3,4-dihydroxyhept-2-yl)amino>-4-<<(1,1-dimethylpropyl)carbonyl>amino>-5-oxopentanoate

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: LiN₃ / dimethylformamide / Ambient temperature

3: 992 mg / Ba(OH)2 / dioxane; H₂O / Heating

4: 1 N aq. HCl / 60 - 65 °C

5: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

6: 44 percent / NaBH₄ / methanol / 0.25 h / 0 °C

7: TFA / CH₂Cl₂ / Ambient temperature

8: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; lithium azide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a005