N^α-tert-butyloxycarbonyl-N^δ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester

Base Information

• Chemical Name: N^α-tert-butyloxycarbonyl-N^δ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester
• CAS No.: 230973-37-2
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495

Synonyms:N^α-tert-butyloxycarbonyl-N^δ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester

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

Chemical Property:

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

There total 6 articles about N^α-tert-butyloxycarbonyl-N^δ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-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: 56.0%

Cα-methyl-3,3-dimethyl-2-(tert-butyloxycarbonylamino)-D-homoglutamate (230973-36-1) + benzyl alcohol (100-51-6,185532-71-2) → Nα-tert-butyloxycarbonyl-Nδ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester (230973-37-2)

Guidance literature:

With TEA; diphenyl-phosphinic acid; In toluene; for 22h; Heating;

DOI:10.1021/jo982474a

Reference yield:

(2R)-3,3-dimethyl-4-oxo-2-<(9-phenylfluoren-9-yl)amino>butyric acid methyl ester (230973-48-5) → Nα-tert-butyloxycarbonyl-Nδ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester (230973-37-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 91 percent / Mg, MeOH / 3 h

3: 1.) NaOH, 2.) NaOH / 2.) Pd/C / 1.) MeOH, reflux, 6 h, 2.) MeOH, EtOAc, 2 atm. 40 h

4: 56 percent / DPPA, TEA / toluene / 22 h / Heating

With methanol; sodium hydroxide; TEA; diphenyl-phosphinic acid; sodium hydride; magnesium; palladium on activated charcoal; In toluene;

DOI:10.1021/jo982474a

Reference yield:

dimethyl-Nα-(9-phenylfluoren-9-yl)-3,3-dimethyl-D-aspartate (230973-45-2) → Nα-tert-butyloxycarbonyl-Nδ-benzyloxycarbonyl-3,3-dimethyl-D-ornithine-methyl ester (230973-37-2)

Guidance literature:

Multi-step reaction with 6 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: 91 percent / Mg, MeOH / 3 h

5: 1.) NaOH, 2.) NaOH / 2.) Pd/C / 1.) MeOH, reflux, 6 h, 2.) MeOH, EtOAc, 2 atm. 40 h

6: 56 percent / DPPA, TEA / toluene / 22 h / Heating

With methanol; sodium hydroxide; TEA; diphenyl-phosphinic acid; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; palladium on activated charcoal; In hexane; dichloromethane; toluene;

DOI:10.1021/jo982474a

upstream raw materials:

C^α-methyl-3,3-dimethyl-2-(tert-butyloxycarbonylamino)-D-homoglutamate

benzyl alcohol

(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

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