N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine

Base Information

• Chemical Name: N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine
• CAS No.: 204061-35-8
• Molecular Formula: C₆₄H₉₃N₅O₈
• Molecular Weight: 1060.47

Synonyms:N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine

Chemical Property of N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine

There total 16 articles about N¹⁵-cholesteryloxycarbonyl-3,7,12-triaza-N^1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine 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: 56.0%

{2-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-ethyl}-carbamic acid benzyl ester (204061-20-1) + {3-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-propyl}-(4-oxo-butyl)-carbamic acid benzyl ester (204061-34-7) → N15-cholesteryloxycarbonyl-3,7,12-triaza-N1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine (204061-35-8)

Guidance literature:

{2-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-ethyl}-carbamic acid benzyl ester; With trimethylphosphane; In tetrahydrofuran; at 20 ℃; for 0.5 - 1h;

{3-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-propyl}-(4-oxo-butyl)-carbamic acid benzyl ester; In tetrahydrofuran; for 3 - 18h;

With sodium tetrahydroborate; In ethanol; diethylene glycol dimethyl ether; at 20 ℃; for 20 - 24h;

Reference yield:

2-(((benzyloxy)carbonyl)amino)ethyl 1-methanesulfonate (134307-72-5) → N15-cholesteryloxycarbonyl-3,7,12-triaza-N1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine (204061-35-8)

Guidance literature:

Multi-step reaction with 8 steps

1: NaBr / dimethylformamide

2: K₂CO₃ / CHCl₃

3: Et₃N, DMAP / CH₂Cl₂

4: Et₃N / CH₂Cl₂ / Ambient temperature

5: 89 percent / TBAF / tetrahydrofuran

6: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

7: NaN₃, NaI / dimethylformamide / 2 h / 80 °C

8: 1.) Me₃P, MS 4A, 2.) NaBH₄ / 1.) THF, 30 min; 1 h, 2.) EtOH, diglyme, 18 h

With dmap; sodium tetrahydroborate; sodium azide; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; sodium iodide; sodium bromide; trimethylphosphane; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3765(199801)4:1<137::AID-CHEM137>3.0.CO;2-2

Reference yield:

Cholesteryl chloroformate (7144-08-3) → N15-cholesteryloxycarbonyl-3,7,12-triaza-N1,3,12-tri(phenylmethoxycarbonyl)pentadecane-1,15-diamine (204061-35-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / CH₂Cl₂ / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

3: NaBr / dimethylformamide / 2 h / 80 °C

4: K₂CO₃ / CHCl₃

5: Et₃N, DMAP / CH₂Cl₂

6: Et₃N / CH₂Cl₂

7: 90 percent / TBAF / tetrahydrofuran

8: 1.) (COCl)2, DMSO, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C to r.t.

9: 1.) Me₃P, MS 4A, 2.) NaBH₄ / 1.) THF, 30 min; 1 h, 2.) EtOH, diglyme, 18 h

With dmap; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bromide; trimethylphosphane; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3765(199801)4:1<137::AID-CHEM137>3.0.CO;2-2

upstream raw materials:

{2-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-ethyl}-carbamic acid benzyl ester

{3-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonylamino]-propyl}-(4-oxo-butyl)-carbamic acid benzyl ester

Cholesteryl chloroformate

benzyl N-(2-bromoethyl)carbamate

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