Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe

Base Information

• Chemical Name: Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe
• CAS No.: 148683-12-9
• Molecular Formula: C₃₂H₄₈N₄O₆S
• Molecular Weight: 616.822
• Mol file: 148683-12-9.mol

Synonyms:

Chemical Property of Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe

There total 12 articles about Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe 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:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe (148683-12-9)

Guidance literature:

Multi-step reaction with 4 steps

2: NaBH₄ / ethanol / 5.5 h / T < -53 deg C

3: 1N aq. NaOH / ethanol / 1) 0 deg C, 30 min, 2) RT, 2 h

4: (EtO)2P(O)CN, NEt₃ / dimethylformamide / 1) 0 deg C, 2 h, 2) RT

With sodium hydroxide; sodium tetrahydroborate; diethyl cyanophosphonate; triethylamine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80547-0

Reference yield:

Boc-L-Pro-H (69610-41-9,117625-90-8) → Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe (148683-12-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NEt₃, Bu₂BOTf / 1) CH₂Cl₂, 2 deg C, 45 min, 2a) CH₂Cl₂, -67 deg C, 2 h, 2b) 12 deg C, 1 h, 2c) RT, 15 min

2: 92 percent / 30percent aq. H₂O₂, 0.4 N aq. LiOH / tetrahydrofuran / 2.5 h / T < 4 deg C

3: (EtO)2P(O)CN, NEt₃ / dimethylformamide / 1) 0 deg C, 2 h, 2) RT

4: TFA / CH₂Cl₂ / Ambient temperature

5: (EtO)2P(O)CN, NEt₃ / dimethylformamide / 1) 0 deg C, 2 h, 2) RT

With lithium hydroxide; diethyl cyanophosphonate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80547-0

Reference yield:

N-(t-butoxycarbonyl)-isoleucine aldehyde (118171-79-2,141321-51-9,141321-54-2,87694-55-1) → Boc-(3R,4S,5S)-bisnorDil-(2R,3R,4S)-norDap-(S)-Doe (148683-12-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) LDA / 1) THF, hexane, -78 deg C, 30 min, 2) THF, -73 deg C, 10 min

2: 1N aq. NaOH / ethanol / 1) 0 deg C, 30 min, 2) RT, 2 h

3: (EtO)2P(O)CN, NEt₃ / dimethylformamide / 1) 0 deg C, 2 h, 2) RT

With sodium hydroxide; diethyl cyanophosphonate; triethylamine; lithium diisopropyl amide; In ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)80547-0

upstream raw materials:

(3R,4S,5S)-4-((tert-butoxycarbonyl)amino)-3-hydroxy-5-methyl-heptanoic acid

N-(tert-butyloxycarbonyl)-L-isoleucine

Boc-L-Pro-H

N-(t-butoxycarbonyl)-isoleucine aldehyde