(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Base Information

• Chemical Name: (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate
• CAS No.: 89985-87-5
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.276
• Hs Code.: 2924199090
• DSSTox Substance ID: DTXSID50431587
• Nikkaji Number: J700.551B
• Wikidata: Q82245506
• Mol file: 89985-87-5.mol

Synonyms:89985-87-5;(S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate;methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pent-4-enoate;(2S)-2-(Boc-amino)-4-pentenoic acid methyl ester;(S)-Methyl 2-(tert-butoxycarbonylamino)pent-4-enoate;Methyl (S)-2-((tert-butoxycarbonyl)amino)pent-4-enoate;MFCD13190790;SCHEMBL614515;(S)-Methyl2-((tert-butoxycarbonyl)amino)pent-4-enoate;DTXSID50431587;APXWRHACXBILLH-QMMMGPOBSA-N;AKOS016843097;AS-69618;CS-0039110;W11819;A928019;A1-50270;(5)-methyl 2-(tert-butoxycarbonylamino)pent-4-enoate;(S)-2-Allyl-N-(tert-butoxycarbonyl)glycine methyl ester;(S)-Methyl 2-(tert-butoxycarbonylamino)-pent-4-enoate;methyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-pentenoate;methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}pent-4-enoate;(S)-Methyl 2-((t-butoxycarbonyl)amino)pent-4-enoate (Boc-Gly(All)-OMe)

Chemical Property of (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Chemical Property:

• Boiling Point: 302.0±35.0 °C(Predicted)
• PKA: 11.08±0.46(Predicted)
• PSA: 64.63000
• Density: 1.035±0.06 g/cm3(Predicted)
• LogP: 2.01970
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 229.13140809
• Heavy Atom Count: 16
• Complexity: 268

Purity/Quality:

99%+, ^*data from raw suppliers

(S)-Methyl 2-(tert-butoxycarbonylamino)-pent-4-enoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC=C)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC=C)C(=O)OC

Technology Process of (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

There total 62 articles about (S)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate 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: 98.0%

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) + diazomethyl-trimethyl-silane (18107-18-1) → methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate (89985-87-5)

Guidance literature:

In methanol; hexane; toluene; for 0.5h;

DOI:10.1016/S0040-4020(02)00541-0

Reference yield: 96.0%

2-((tert-butyloxycarbonyl)amino)-4-pentenoic acid (119479-32-2) + methyl iodide (74-88-4) → methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate (89985-87-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/acs.joc.7b01135

Reference yield: 95.0%

L-allylglycine (16338-48-0) + di-tert-butyl dicarbonate (24424-99-5) → methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate (89985-87-5)

Guidance literature:

L-allylglycine; di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane; water; at 0 ℃; for 16h;

With hydrogenchloride; In 1,4-dioxane; water; pH=2;

With potassium carbonate; methyl iodide; more than 3 stages;

upstream raw materials:

diazomethane

L-allylglycine

2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile

vinyllithium

Downstream raw materials:

methyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pentanoate

(S)-tert-butyl (1-hydroxypent-4-en-2-yl)carbamate

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(2S)-2-[(tert-butoxycarbonyl)amino]hept-6-enoic acid

Refernces

• 1、 Ohfune, Yasufumi,Nishio, Hideki. "ACYCLIC STEREOCONTROLLED SYNTHESIS OF (-)-DETOXININE". . p. 4133 - 4136. Retrieved 1984.
• 2、 Vitkovska, Viktorija,Zogota, Rimants,Kalnins, Toms,Zelencova, Diana,Suna, Edgars. "Aliphatic chain-containing macrocycles as diazonamide A analogs". . p. 586 - 602. Retrieved 2020/06/10.