(R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate

Base Information

• Chemical Name: (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate
• CAS No.: 176966-00-0
• Molecular Formula: C₁₈H₁₅NO₅
• Molecular Weight: 325.321
• Mol file: 176966-00-0.mol

Synonyms:(R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate

Chemical Property of (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate

There total 2 articles about (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate 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: 20.0%

(S)-(-)-3-butyn-2-ol (2914-69-4) + N,O-Bis(phenoxycarbonyl)hydroxylamine (141580-65-6) → (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate (176966-00-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.0c00561

Reference yield: 20.0%

→ (R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate (176966-00-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

Reference yield:

(R)-phenyl but-3-yn-2-yl((phenoxycarbonyl)oxy)carbamate (176966-00-0) → (R)-N-(3-butyn-2-yl)-N-carbamoyl-O-(S)-α-methoxyphenylacetylhydroxylamine

Guidance literature:

Multi-step reaction with 2 steps

1: conc. NH₄OH / methanol / 24 h / Ambient temperature

2: CDI / CH₂Cl₂ / 14 h / Ambient temperature

With ammonium hydroxide; 1,1'-carbonyldiimidazole; In methanol; dichloromethane;

DOI:10.1016/0957-4166(96)00068-7

upstream raw materials:

(S)-(-)-3-butyn-2-ol

N,O-Bis(phenoxycarbonyl)hydroxylamine

Refernces

• 1、 Hiesinger, Kerstin,Kramer, Jan S.,Beyer, Sandra,Eckes, Timon,Brunst, Steffen,Flauaus, Cathrin,Wittmann, Sandra K.,Weizel, Lilia,Kaiser, Astrid,Kretschmer, Simon B. M.,George, Sven,Angioni, Carlo,Heering, Jan,Geisslinger, Gerd,Schubert-Zsilavecz, Manfred,Schmidtko, Achim,Pogoryelov, Denys,Pfeilschifter, Josef,Hofmann, Bettina,Steinhilber, Dieter,Schwalm, Stephanie,Proschak, Ewgenij. "Design, Synthesis, and Structure-Activity Relationship Studies of Dual Inhibitors of Soluble Epoxide Hydrolase and 5-Lipoxygenase". . p. 11498 - 11521. Retrieved 2020/11/03.