D-ASPARTIC ACID, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-, 4-(2-PROPENYL) ESTER

Base Information

• Chemical Name: D-ASPARTIC ACID, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-, 4-(2-PROPENYL) ESTER
• CAS No.: 207120-58-9
• Molecular Formula: C₁₂H₁₉NO₆
• Molecular Weight: 273.286
• Mol file: 207120-58-9.mol

Synonyms:(R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Chemical Property of D-ASPARTIC ACID, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-, 4-(2-PROPENYL) ESTER

Chemical Property:

• Boiling Point: 437.6±45.0 °C(Predicted)
• PKA: 3.70±0.23(Predicted)
• Density: 1.175±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-d-asp(oall)-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-ASPARTIC ACID, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-, 4-(2-PROPENYL) ESTER

There total 2 articles about D-ASPARTIC ACID, N-[(1,1-DIMETHYLETHOXY)CARBONYL]-, 4-(2-PROPENYL) 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: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + β-allyl (2R)-aspartate ester hydrochloride → (R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (207120-58-9)

Guidance literature:

With water; triethylamine; In 1,4-dioxane; for 18h;

DOI:10.1039/b100401h

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + 2-amino-succinic acid 4-allyl ester → (R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (207120-58-9)

Guidance literature:

di-tert-butyl dicarbonate; 2-amino-succinic acid 4-allyl ester; In 1,4-dioxane; water;

With triethylamine; In 1,4-dioxane; water;

DOI:10.1021/jm301058f

Reference yield: 94.0%

(S)-N-benzylserine methyl ester (123639-56-5) + (R)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (207120-58-9) → 4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate (1389331-94-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.201200457

upstream raw materials:

di-tert-butyl dicarbonate

Downstream raw materials:

β-allyl α-benzyl (2R)-N-(tert-butoxycarbonyl)aspartate diester

β-allyl α-benzyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-(2R)-aspartate diester

β-allyl (2S)-N-(tert-butoxycarbonyl)phenylalanyl-[α-benzyl (2R)-aspartyl]-β-[α-methyl (2R)-glutamyl]-γ-sarcosyl-[α-methyl (2R)-aspartate] tetraester

4-allyl 1-[(2S)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-D-aspartate

Refernces

• 1、 Webster,Maude,O'Donnell,Mehrotra,Gani. "Design and preparation of serine-threonine protein phosphatase inhibitors based upon the nodularin and microcystin toxin structures. Part 3". . p. 1673 - 1695. Retrieved 2007/10/03.