(2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid

Base Information

• Chemical Name: (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid
• CAS No.: 815584-72-6
• Molecular Formula: C₂₈H₃₆N₂O₈
• Molecular Weight: 528.602
• Mol file: 815584-72-6.mol

Synonyms:(2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid

Chemical Property of (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid

There total 11 articles about (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid 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: 92.0%

(2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate (815584-71-5) → (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid (815584-72-6)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium dihydrogenphosphate; sodium chlorite; In acetonitrile; at 40 ℃; for 18h; pH=6.7;

DOI:10.1021/jo0485738

Reference yield:

(S)-2-(Benzyl-benzyloxycarbonyl-amino)-pent-4-enoic acid methyl ester → (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid (815584-72-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 0.82 g / aq. NaOH / methanol / 3 h

2: PyBOP; Et₃N / CH₂Cl₂ / 16 h / 20 °C

3: 0.89 g / pyridine / CH₂Cl₂ / 1 h

4: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

5: 99 percent / Grubb's second-generation catalyst / CH₂Cl₂ / 2 h / Heating

6: aq. LiOH / tetrahydrofuran / 24 h / 20 °C

7: K₂CO₃ / dimethylformamide / 5 h / 20 °C

8: 168 mg / H₂ / [Ir(COD)PyPCy₃]PF₆ / CH₂Cl₂ / 16 h / 760 Torr

9: 92 percent / aq. NaH₂PO₄; TEMPO; NaOCl / NaClO₂ / acetonitrile / 18 h / 40 °C / pH 6.7

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hydroxide; sodium hypochlorite; sodium dihydrogenphosphate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; potassium carbonate; triethylamine; sodium chlorite; Crabtree's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0485738

Reference yield:

(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate (815584-68-0) → (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid (815584-72-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 77 percent / DMAP / tetrahydrofuran / 20 h / 20 °C

2: 99 percent / Grubb's second-generation catalyst / CH₂Cl₂ / 2 h / Heating

3: aq. LiOH / tetrahydrofuran / 24 h / 20 °C

4: K₂CO₃ / dimethylformamide / 5 h / 20 °C

5: 168 mg / H₂ / [Ir(COD)PyPCy₃]PF₆ / CH₂Cl₂ / 16 h / 760 Torr

6: 92 percent / aq. NaH₂PO₄; TEMPO; NaOCl / NaClO₂ / acetonitrile / 18 h / 40 °C / pH 6.7

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; sodium dihydrogenphosphate; hydrogen; potassium carbonate; sodium chlorite; Crabtree's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo0485738

upstream raw materials:

(2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate

(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)aminopent-4-enamido)but-3-enyl acetate

(3S,7R)-7-Acetoxymethyl-3-(benzyl-benzyloxycarbonyl-amino)-2-oxo-2,3,4,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester

(R)-2-((S)-2-(N-benzyl-N-benzyloxycarbonyl)amino-(N-tert-butoxycarbonyl)pent-4-enamido)but-3-enyl acetate