N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester

Base Information

• Chemical Name: N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester
• CAS No.: 230973-53-2
• Molecular Formula: C₂₂H₃₄N₂O₆
• Molecular Weight: 422.522

Synonyms:N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester

Chemical Property of N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester

There total 8 articles about N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester 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:

(2R)-3,3-dimethyl-4-oxo-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester (230973-48-5) → Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester (230973-53-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DME, 0 deg C, 15 min, 2.) DME, room temperature, 3 h

2: 93 percent / DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -45 °C

3: 1.) TEA, 2-fluoro-N-methylpyridinium tosylate, 2.) LiN₃ / 1.) CHCl₃, 2.) HMPA, 90 deg C, 15 h

4: 1.) PPh₃, 2.) H₂O / 1.) THF, 65 deg C, 22 h, 2.) 22 h

5: NaHCO₃ / dioxane / 6 h

6: H₂ / Pd/C / methanol; ethyl acetate / 16 h / 1520 Torr

7: NMM / CH₂Cl₂ / 18 h

With 4-methyl-morpholine; lithium azide; TEA; water; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo982474a

Reference yield:

dimethyl-Nα-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate (230973-45-2) → Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester (230973-53-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 65 percent / DIBAL-H / CH₂Cl₂; hexane / 3 h / -40 °C

2: Dess-Martin periodinane / 2 h / Ambient temperature

3: 1.) NaH / 1.) DME, 0 deg C, 15 min, 2.) DME, room temperature, 3 h

4: 93 percent / DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -45 °C

5: 1.) TEA, 2-fluoro-N-methylpyridinium tosylate, 2.) LiN₃ / 1.) CHCl₃, 2.) HMPA, 90 deg C, 15 h

6: 1.) PPh₃, 2.) H₂O / 1.) THF, 65 deg C, 22 h, 2.) 22 h

7: NaHCO₃ / dioxane / 6 h

8: H₂ / Pd/C / methanol; ethyl acetate / 16 h / 1520 Torr

9: NMM / CH₂Cl₂ / 18 h

With 4-methyl-morpholine; lithium azide; TEA; water; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; Dess-Martin periodane; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo982474a

Reference yield:

(2R)-3,3-dimethyl-4-hydroxy-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester (230973-46-3) → Nα-benzyloxycarbonyl-Nε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine methyl ester (230973-53-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Dess-Martin periodinane / 2 h / Ambient temperature

2: 1.) NaH / 1.) DME, 0 deg C, 15 min, 2.) DME, room temperature, 3 h

3: 93 percent / DIBAL-H / CH₂Cl₂; hexane / 0.25 h / -45 °C

4: 1.) TEA, 2-fluoro-N-methylpyridinium tosylate, 2.) LiN₃ / 1.) CHCl₃, 2.) HMPA, 90 deg C, 15 h

5: 1.) PPh₃, 2.) H₂O / 1.) THF, 65 deg C, 22 h, 2.) 22 h

6: NaHCO₃ / dioxane / 6 h

7: H₂ / Pd/C / methanol; ethyl acetate / 16 h / 1520 Torr

8: NMM / CH₂Cl₂ / 18 h

With 4-methyl-morpholine; lithium azide; TEA; water; hydrogen; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; Dess-Martin periodane; triphenylphosphine; palladium on activated charcoal; In 1,4-dioxane; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo982474a

upstream raw materials:

(2R)-3,3-dimethyl-4-oxo-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester

dimethyl-N^α-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate

(2R)-3,3-dimethyl-4-hydroxy-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester

methyl-(2R)-3,3-dimethyl-6-hydroxy-2-<(9-phenylfluoren-9-yl)amino>-4-hexenoate

Downstream raw materials:

N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyl-3,3-dimethyl-D-lysine

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