<1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide

Base Information

• Chemical Name: <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide
• CAS No.: 135703-97-8
• Molecular Formula: C₃₂H₅₀N₆O₇S₂
• Molecular Weight: 694.917

Synonyms:

Chemical Property of <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide

There total 9 articles about <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide 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: 42.0%

(4-{((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-methyl}-thiazol-2-yl)-carbamic acid benzyl ester (135704-13-1,142185-77-1,142185-78-2) → <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide (135703-97-8,142185-71-5,142234-98-8)

Guidance literature:

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; for 6h; Ambient temperature;

DOI:10.1021/jm00092a006

Reference yield:

ethyl 2-amino-α-(N-(t-butoxycarbonyl)amino)-4-thiazoleacetate (60846-29-9) → <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide (135703-97-8,142185-71-5,142234-98-8)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. sodium bicarbonate / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

2: aq. KOH / ethanol / 1.5 h / Ambient temperature

3: 6.0 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

4: 5.5 g / HCl (gas) / methanol / Ambient temperature

5: 3.4 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

6: 42 percent / H₂, p-toluenesulfonic acid hydrate / 20percent Pd/C / methanol / 6 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

Reference yield:

ethyl α-(2-benzyloxycarbonylaminothiazol-4-yl)-α-(t-butoxycarbonylamino)acetate (92592-16-0) → <1S-<1R*,2S*,3R*>>-2-amino-N-<1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl>-α-<<2-<(4-morpholinylsulfonyl)amino>-1-oxo-3-phenylpropyl>amino>-3-thiazoleacetamide (135703-97-8,142185-71-5,142234-98-8)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. KOH / ethanol / 1.5 h / Ambient temperature

2: 6.0 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

3: 5.5 g / HCl (gas) / methanol / Ambient temperature

4: 3.4 g / N-hydroxybenzotriazole (HOBT), dicyclohexylcarbodiimide (DCC), triethylamine / dimethylformamide / 0 - 20 °C

5: 42 percent / H₂, p-toluenesulfonic acid hydrate / 20percent Pd/C / methanol / 6 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00092a006

upstream raw materials:

(4-{((1S,2R,3S)-1-Cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-[(S)-2-(morpholine-4-sulfonylamino)-3-phenyl-propionylamino]-methyl}-thiazol-2-yl)-carbamic acid benzyl ester

ethyl 2-amino-α-(N-(t-butoxycarbonyl)amino)-4-thiazoleacetate

N-(4-MorpholinYlsulfonyl)-L-phenylalanine

α-(2-benzyloxycarbonylaminothiazol-4-yl)-α-(t-butoxycarbonylamino)acetic acid

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