Cbz-[(R,R)-Ac₅c(dOM)]4-OMe

Base Information

• Chemical Name: Cbz-[(R,R)-Ac₅c(dOM)]4-OMe
• CAS No.: 1380078-04-5
• Molecular Formula: C₄₁H₆₂N₄O₁₅
• Molecular Weight: 850.961
• Mol file: 1380078-04-5.mol

Synonyms:

Chemical Property of Cbz-[(R,R)-Ac₅c(dOM)]4-OMe

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cbz-[(R,R)-Ac₅c(dOM)]4-OMe

There total 12 articles about Cbz-[(R,R)-Ac₅c(dOM)]4-OMe 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:

C17H30N2O7 + (3R,4R)-3,4-dimethoxy-1-{[(3R,4R)-3,4-dimethoxy-1-(benzyloxycarbonylamino)-cyclopentyl]carbonylamino}cyclopentanecarboxylic acid (1380078-03-4) → Cbz-[(R,R)-Ac5c(dOM)]4-OMe (1380078-04-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 20 ℃; for 90h;

DOI:10.1002/chem.201102902

Reference yield:

(2S,3S)-1,4-diiodo-2,3-dimethoxybutane (1379793-07-3) → Cbz-[(R,R)-Ac5c(dOM)]4-OMe (1380078-04-5)

Guidance literature:

Multi-step reaction with 9 steps

1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

2: sodium hydroxide / methanol; water / 5 h / 0 °C

3: diphenyl phosphoryl azide; triethylamine / benzene

4: benzene / 1 h / Reflux

5: benzene / 6 h / Reflux

6: sodium hydroxide / methanol; water / 12 h / 20 °C

7: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 60 h / 20 °C

8: sodium hydroxide / methanol; water / 12 h / 20 °C

9: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 90 h / 20 °C

With diphenyl phosphoryl azide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide; acetonitrile; benzene; 4: Curtius rearrangement;

DOI:10.1002/chem.201102902

Reference yield:

methyl (3R,4R)-3,4-dimethoxy-1-(methoxycarbonyl)cyclopentanecarboxylate (1379793-08-4) → Cbz-[(R,R)-Ac5c(dOM)]4-OMe (1380078-04-5)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide / methanol; water / 5 h / 0 °C

2: diphenyl phosphoryl azide; triethylamine / benzene

3: benzene / 1 h / Reflux

4: benzene / 6 h / Reflux

5: sodium hydroxide / methanol; water / 12 h / 20 °C

6: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 60 h / 20 °C

7: 5%-palladium/activated carbon; hydrogen / methanol

8: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile / 90 h / 20 °C

With diphenyl phosphoryl azide; 5%-palladium/activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol; water; acetonitrile; benzene; 3: Curtius rearrangement;

DOI:10.1002/chem.201102902

upstream raw materials:

H-(R,R)-Ac₅cdOM-OMe

(2S,3S)-1,4-diiodo-2,3-dimethoxybutane

methyl (3R,4R)-3,4-dimethoxy-1-(methoxycarbonyl)cyclopentanecarboxylate

C₁₀H₁₆O₆

Downstream raw materials:

Cbz-[(R,R)-Ac₅c(dOM)]6-OMe