(3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene

Base Information

• Chemical Name: (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene
• CAS No.: 619328-41-5
• Molecular Formula: C₁₆H₂₃NO₂S
• Molecular Weight: 293.43
• Mol file: 619328-41-5.mol

Synonyms:(3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene

Chemical Property of (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene

There total 5 articles about (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene 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: 55.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)aminopropionaldehyde (118546-67-1) → (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene (619328-41-5)

Guidance literature:

With n-butyllithium; potassium hexamethylsilazane; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1039/b306124h

Reference yield: 55.0%

Methyltriphenylphosphonium bromide (1779-49-3) + S-Benzyl-Nα-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide (208521-21-5) → (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene (619328-41-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

S-Benzyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide; In tetrahydrofuran; toluene; at -78 - 20 ℃;

DOI:10.1039/b404205k

Reference yield:

S-benzyl-L-cysteine (3054-01-1,25988-62-9) → (3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)amino-1-butene (619328-41-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / Et₃N

2.1: 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 0.25 h / 20 °C

2.2: 84 percent / (i-Pr)2NH / tetrahydrofuran / 12 h / 20 °C

3.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: 55 percent / tetrahydrofuran; toluene / -78 - 20 °C

With potassium hexamethylsilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; toluene; 3.2: Wittig olefination;

DOI:10.1039/b404205k

upstream raw materials:

Methyltriphenylphosphonium bromide

(3R)-4-benzylthio-3-(N-tert-butyloxycarbonyl)aminopropionaldehyde

S-Benzyl-N_α-(tert-butyloxycarbonyl)-cysteine-N-methoxy-N-methylamide

S-benzyl-L-cysteine

Downstream raw materials:

(1''R,2'R,3R,4S,6S)-3,4,6-trimethyl-8-[methyl-(2'-methylbutyryl)amino]octanoic acid (1''-benzylsulfanylmethylallyl)amide

benzyl (R)-2-amino-3-butenyl sulfide

Refernces

• 1、 White, James D.,Xu, Qing,Lee, Chang-Sun,Valeriote, Frederick A.. "Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula". . p. 2092 - 2102. Retrieved 2007/10/03.