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

Base Information

• Chemical Name: (3S,5R)-5-[N¹-[3-(N²-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene
• CAS No.: 796039-27-5
• Molecular Formula: C₂₄H₄₂N₂O₅Si
• Molecular Weight: 466.693

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

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

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

There total 1 articles about (3S,5R)-5-[N¹-[3-(N²-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene 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: 67.0%

di-tert-butyl dicarbonate (24424-99-5) + tert-butyldimethylsilyl chloride (18162-48-6) + (3-Amino-propyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester (190264-78-9) → (3S,5R)-5-[N1-[3-(N2-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-27-5)

Guidance literature:

tert-butyldimethylsilyl chloride; (3-Amino-propyl)-carbamic acid (1R,5S)-3-ethynyl-5-hydroxy-4-methyl-cyclohex-3-enyl ester; With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 12h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In chloroform; at 20 ℃; for 3h;

DOI:10.1016/j.bmc.2004.07.042

Reference yield:

25-trimethylsilyloxy-de-A,B-cholest-8-en-8-yl trifluoromethanesulfonate (222317-53-5) + (3S,5R)-5-[N1-[3-(N2-tert-butyloxycarbonylaminopropyl)carbamoyl]oxy]-3-[(tert-butyldimethylsilyl)oxy]-1-ethynyl-2-methylcyclohex-1-ene (796039-27-5) → (3-{(1R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[(1R,3aR,7aR)-1-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-ylethynyl]-4-methyl-cyclohex-3-enyloxycarbonylamino}-propyl)-carbamic acid tert-butyl ester

Guidance literature:

With copper(l) iodide; diethylamine; bis(triphenylphosphine) palladium (Il) acetate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

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-((1R,5S)-5-Hydroxy-3-{(Z)-2-[(1R,3aR,7aR)-1-((R)-5-hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methyl-cyclohex-3-enyloxycarbonylamino)-propyl]-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 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

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;

DOI:10.1016/j.bmc.2004.07.042

upstream raw materials:

di-tert-butyl dicarbonate

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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

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