1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol

Base Information

• Chemical Name: 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol
• CAS No.: 690629-94-8
• Molecular Formula: C₂₇H₄₅NO₅Si
• Molecular Weight: 491.744

Synonyms:1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol

Chemical Property of 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol

Chemical Property:

Purity/Quality:

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Technology Process of 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol

There total 3 articles about 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol 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: 79.0%

N-Boc-D-Leu (16937-99-8,53296-34-7) + 2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-4-methylphenol (300767-38-8) → 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol (690629-94-8)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bioorg.2003.12.002

Reference yield:

2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol (51765-10-7) → 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol (690629-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-(dimethylamino)pyridine / 0 °C

2: 79 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.bioorg.2003.12.002

Reference yield:

6-methylcoumarin (92-48-8) → 1-O-(N-Boc-D-leucyl)-2-[(Z)-3-(1-tert-butyl-1,1-dimethylsilyloxy)-1-propenyl]-4-methylphenol (690629-94-8)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminum hydride

2: 4-(dimethylamino)pyridine / 0 °C

3: 79 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

With dmap; lithium aluminium tetrahydride; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/j.bioorg.2003.12.002

upstream raw materials:

N-Boc-D-Leu

2-[(Z)-3-{[1-(tert-butyl)-1,1-dimethyl-silanyl]oxy}-1-propenyl]-4-methylphenol

2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol

6-methylcoumarin

Downstream raw materials:

(R)-2-tert-Butoxycarbonylamino-4-methyl-pentanoic acid 2-{(Z)-2-[(S)-1-((R)-1-{[((S)-1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-carbamoyl}-ethylcarbamoyl)-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-vinyl}-4-methyl-phenyl ester

(Z)-3-[2-(1-N-Boc-D-leucyl)-4-methylphenyl]-2-propenoic acid

1-O-(N-Boc-D-leucyl)-4-methyl-2-[(Z)-3-oxo-1-propenyl]phenol

1-O-(N-Boc-D-leucyl)-2-[(Z)-3-hydroxy-1-propenyl]-4-methylphenol

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