Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide

Base Information

• Chemical Name: Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide
• CAS No.: 400611-25-8
• Molecular Formula: C17H25 N O4 S
• Molecular Weight: 339.456
• Mol file: 400611-25-8.mol

Synonyms:Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide;Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide (9CI)

Chemical Property of Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide

Chemical Property:

• Melting Point: 163 °C

Purity/Quality:

98% ^*data from raw suppliers

DIMETHYL-(3S)-3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-OXO-4-PHENYLBUTYLIDE SULFOXONIUM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide

There total 10 articles about Sulfoxonium, dimethyl-, (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-oxo-4-phenylbutylide 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%

trimethylsulfoxonium iodide (1774-47-6) + C19H27NO5 → tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate (400611-25-8)

Guidance literature:

trimethylsulfoxonium iodide; With potassium tert-butylate; In tetrahydrofuran; at 90 ℃; for 2h;

C₁₉H₂₇NO₅; In tetrahydrofuran; at -20 ℃;

Reference yield: 80.0%

→ tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate (400611-25-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 3h; Reflux; Darkness;

In tetrahydrofuran; at 0 ℃; for 18h;

Reference yield: 79.0%

Boc-Phe-O-COO-isoBu (67729-36-6,60398-40-5) + trimethylsulfoxonium iodide (1774-47-6) → tert-butyl (S)-(4-(dimethyl(oxo)-λ6-sulfanylidene)-3-oxo-1-phenylbutan-2-yl)carbamate (400611-25-8)

Guidance literature:

trimethylsulfoxonium iodide; With potassium tert-butylate; In tetrahydrofuran; at 90 ℃; for 2h;

Boc-Phe-O-COO-isoBu; In tetrahydrofuran; at 0 ℃; for 2.75h; Product distribution / selectivity;

upstream raw materials:

N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester

trimethylsulfoxonium iodide

C₁₈H₂₈NO₇P

Boc-Phe-O-COO-isoBu

Downstream raw materials:

C₂₂H₂₇NO₄

C₂₁H₂₆N₂O₃

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

(1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester

Refernces

• 1、 -. "SULFOXONIUM YLIDE DERIVATIVES AS PROBES FOR CYSTEINE PROTEASE". Paragraph 0368; 0398-0401; 0411-0413. . Retrieved 2020/07/14.
• 2、 Wang, Dengjin,Schwinden, Mark D.,Radesca, Lilian,Patel, Bharat,Kronenthal, David,Huang, Ming-Hsing,Nugent, William A.. "One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane". . p. 1629 - 1633. Retrieved 2007/10/03.