3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3

Base Information

• Chemical Name: 3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3
• CAS No.: 796039-24-2
• Molecular Formula: C₃₆H₆₀N₂O₆
• Molecular Weight: 616.882

Synonyms:3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3

Chemical Property of 3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3

Chemical Property:

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Technology Process of 3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3

There total 5 articles about 3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3 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:

di-tert-butyl dicarbonate (24424-99-5) → 3-O-[N1-(3-N2-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3 (796039-24-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

1.2: 67 percent / aq. NaHCO₃ / CHCl₃ / 3 h / 20 °C

2.1: CuI; Et₂NH / Pd(PPh₃)2(OAc)2 / dimethylformamide / 1 h / 20 °C

3.1: TBAF / tetrahydrofuran / 12 h / 20 °C

4.1: H₂; quinoline / Lindlar catalyst / methanol; hexane / 1 h / 20 °C

5.1: acetone / 4 h / 80 °C

With 1H-imidazole; quinoline; dmap; copper(l) iodide; tetrabutyl ammonium fluoride; hydrogen; diethylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2004.07.042

Reference yield:

(3-Amino-propyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester (190264-78-9) → 3-O-[N1-(3-N2-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3 (796039-24-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

1.2: 67 percent / aq. NaHCO₃ / CHCl₃ / 3 h / 20 °C

2.1: CuI; Et₂NH / Pd(PPh₃)2(OAc)2 / dimethylformamide / 1 h / 20 °C

3.1: TBAF / tetrahydrofuran / 12 h / 20 °C

4.1: H₂; quinoline / Lindlar catalyst / methanol; hexane / 1 h / 20 °C

5.1: acetone / 4 h / 80 °C

With 1H-imidazole; quinoline; dmap; copper(l) iodide; tetrabutyl ammonium fluoride; hydrogen; diethylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2004.07.042

Reference yield:

(3S,5R)-5-[N1-[3-(N2-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-27-5) → 3-O-[N1-(3-N2-tert-butyloxycarbonylaminopropyl)carbamoyl]-1α,25-dihydroxyvitamin D3 (796039-24-2)

Guidance literature:

Multi-step reaction with 4 steps

1: CuI; Et₂NH / Pd(PPh₃)2(OAc)2 / dimethylformamide / 1 h / 20 °C

2: TBAF / tetrahydrofuran / 12 h / 20 °C

3: H₂; quinoline / Lindlar catalyst / methanol; hexane / 1 h / 20 °C

4: acetone / 4 h / 80 °C

With quinoline; copper(l) iodide; tetrabutyl ammonium fluoride; hydrogen; diethylamine; Lindlar's catalyst; bis(triphenylphosphine) palladium (Il) acetate; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmc.2004.07.042

upstream raw materials:

di-tert-butyl dicarbonate

(3-Amino-propyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester

(3S,5R)-5-[N¹-[3-(N²-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene

3-O-[N¹-(3-N²-tert-butyloxycarbonylaminopropyl)carbamoyl]-6,7-dehydro-1α,25-dihydroxyvitamin D3

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