(1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid

Base Information

• Chemical Name: (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid
• CAS No.: 1017279-82-1
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 1017279-82-1.mol

Synonyms:(1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid

Chemical Property of (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid

There total 7 articles about (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid 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: 94.0%

benzyl (1R,3S)-3-tert-butoxycarbonyl-2,2-dimethylcyclobutyl-1-carbamate (1017279-80-9) → (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid (1017279-82-1)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane;

DOI:10.1007/s00726-011-0912-4

Reference yield:

benzyl ((1R,3S)-3-(hydroxymethyl)-2,2-dimethylcyclobutyl)carbamate → (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid (1017279-82-1)

Guidance literature:

With sodium periodate; ruthenium(III) chloride hydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 1h;

Reference yield:

(1S,3R)-3-acetyl-2,2-dimethylcyclobutane carboxylic acid (288848-24-8) → (1S,3R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutanecarboxylic acid (1017279-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / tetrahydrofuran / 0 °C

2.1: sodium hypobromide / 1,4-dioxane; water

3.3: Reflux

4.1: triethylsilane; trifluoroacetic acid / dichloromethane

With triethylsilane; dmap; sodium hypobromide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1007/s00726-011-0912-4

upstream raw materials:

benzyl (1R,3S)-3-tert-butoxycarbonyl-2,2-dimethylcyclobutyl-1-carbamate

(-)-Verbenone

(1S,3R)-3-acetyl-2,2-dimethylcyclobutane carboxylic acid

tert-butyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate

Downstream raw materials:

benzyl (1R,3S)-3-methoxycarbonyl-2,2-dimethylcyclobutyl-1-carbamate

C₂₆H₃₈N₂O₅

C₂₅H₃₅N₃O₇

C₄₃H₆₄N₆O₁₁