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

Base Information

• Chemical Name: (2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate
• CAS No.: 815584-71-5
• Molecular Formula: C₂₈H₃₈N₂O₇
• Molecular Weight: 514.619
• Mol file: 815584-71-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate 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:

(Z)-(2S,6R)-2-(Benzyl-benzyloxycarbonyl-amino)-6-tert-butoxycarbonylamino-7-hydroxy-hept-4-enoic acid methyl ester → (2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate (815584-71-5)

Guidance literature:

With hydrogen; Crabtree's catalyst; In dichloromethane; for 16h; under 760 Torr;

DOI:10.1021/jo0485738

Reference yield:

(S)-2-(Benzyl-benzyloxycarbonyl-amino)-pent-4-enoic acid methyl ester → (2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate (815584-71-5)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/jo0485738

Reference yield:

(Z)-(2S,6R)-2-(Benzyl-benzyloxycarbonyl-amino)-6-tert-butoxycarbonylamino-7-hydroxy-hept-4-enoic acid → (2S,6R)-methyl 2-(N-benzyl-N-benzyloxycarbonyl)amino-6-(N-tert-butoxycarbonyl)amino-7-hydroxyheptanoate (815584-71-5)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 168 mg / H₂ / [Ir(COD)PyPCy₃]PF₆ / CH₂Cl₂ / 16 h / 760 Torr

With hydrogen; potassium carbonate; Crabtree's catalyst; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0485738

upstream raw materials:

(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

(S)-2--4-pentenoic Acid

Downstream raw materials:

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