(2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester

Base Information

• Chemical Name: (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester
• CAS No.: 82876-05-9
• Molecular Formula: C₂₁H₃₀N₂O₈
• Molecular Weight: 438.478
• Mol file: 82876-05-9.mol

Synonyms:(2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester

Chemical Property of (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester

There total 9 articles about (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-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: 75.0%

(2R,6S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-7-hydroxy-heptanoic acid methyl ester (144619-42-1) → (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester (82876-05-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61270-4

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester (82876-05-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 20 percent / n-BuLi / tetrahydrofuran

2: 95 percent / CBr₄, PPh₃ / CH₂Cl₂ / 0 °C

3: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

4: 48 percent / 0.1N aq.HCl / tetrahydrofuran

5: H₂ / Pd/C / ethyl acetate

6: 84 percent / NaHCO₃ / diethyl ether

7: 91 percent / p-TsOH, H₂O / methanol

8: 75 percent / pyridinium dichromate (PDC) / dimethylformamide

With hydrogenchloride; dipyridinium dichromate; n-butyllithium; carbon tetrabromide; water; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61270-4

Reference yield:

(S)-((1E)-3-hydroxy-propenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (130532-54-6) → (2S,6R)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-heptanedioic acid 1-methyl ester (82876-05-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / CBr₄, PPh₃ / CH₂Cl₂ / 0 °C

2: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

3: 48 percent / 0.1N aq.HCl / tetrahydrofuran

4: H₂ / Pd/C / ethyl acetate

5: 84 percent / NaHCO₃ / diethyl ether

6: 91 percent / p-TsOH, H₂O / methanol

7: 75 percent / pyridinium dichromate (PDC) / dimethylformamide

With hydrogenchloride; dipyridinium dichromate; n-butyllithium; carbon tetrabromide; water; hydrogen; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)61270-4

upstream raw materials:

(2R,6S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-7-hydroxy-heptanoic acid methyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

(S)-((1E)-3-hydroxy-propenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S,E)-tert-butyl 4-(3-bromoprop-1-enyl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

(2R,6S)-2-Benzyloxycarbonylamino-6-[(S)-1-((R)-3-benzyloxycarbonyl-1-carbamoyl-propylcarbamoyl)-ethylcarbamoyl]-6-tert-butoxycarbonylamino-hexanoic acid methyl ester