Sarkomycin

Base Information

• Chemical Name: Sarkomycin
• CAS No.: 11031-48-4
• Deprecated CAS: 1404-60-0,13012-37-8
• Molecular Formula: C7H8O3
• Molecular Weight: 140.15
• UNII: UA4DEJ83YR
• Nikkaji Number: J175.454H
• Wikidata: Q27290975
• Mol file: 11031-48-4.mol

Synonyms:sarkomycin A;sarkomycin A, sodium salt

Chemical Property of Sarkomycin

Chemical Property:

• Vapor Pressure: 6.65E-05mmHg at 25°C
• Refractive Index: 1.4850 (estimate)
• Boiling Point: 320.3°Cat760mmHg
• Flash Point: 161.8°C
• Density: 1.23g/cm³
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 205

Purity/Quality:

98%,99%, ^*data from raw suppliers

SARKOMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=C1C(CCC1=O)C(=O)O
• Isomeric SMILES: C=C1[C@H](CCC1=O)C(=O)O

Technology Process of Sarkomycin

There total 89 articles about Sarkomycin 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: 86.0%

(2R)-(tetrahydropyran-2-yloxymethyl)cyclopentanone-(3R)-carboxylic acid (1469357-21-8) → sarkomycin (69274-56-2,72581-31-8,143954-86-3,489-21-4,11031-48-4)

Guidance literature:

With ion-exchange resin Lewatit K₂₆₁₁; In acetone; at 60 ℃; for 1h; Solvent; Reagent/catalyst; Temperature; Time; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jo4016979

Reference yield: 80.0%

3-<(phenylthio)dichloromethyl>-2-methylenecyclopentanone (96258-20-7) → sarkomycin (72581-31-8,11031-48-4) + sarkomycin phenyl thio ester (96258-21-8)

Guidance literature:

With 3-methyl-4-hydroxy-5-tert-butylbenzenethiol; silver trifluoroacetate; In tetrahydrofuran; water; at 25 ℃; for 2h;

DOI:10.1021/jo00216a031

Reference yield: 45.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-Diethoxyphosphoryl-3-carboxy-cyclopentanone (123444-59-7) → sarkomycin (72581-31-8,11031-48-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1016/S0040-4039(01)80382-8

upstream raw materials:

ethyl 3-oxocyclopentanecarboxylate

formaldehyd

2-Diethoxyphosphoryl-3-carboxy-cyclopentanone

6-Methoxymethyl-1,4-dioxa-spiro[4.4]nonane-7-carboxylic acid methyl ester

Downstream raw materials:

2-methyl-2-cyclopenten-1-one-3-carboxylic acid

methyl (-)-trans-2-methylcyclopentan-3-one-1-carboxylate

Refernces

• 1、 Kobayashi,Tsuji. "Simple total synthesis of sarkomycin". . p. 4295 - 4296. Retrieved 1981.
• 2、 Hill,R.K. et al.. "-". . p. 2330 - 2335. Retrieved 1967.
• 3、 Boeckman, Robert K.,Naegely, Paul C.,Arthur, Samuel D.. "Efficient Enantioselective Synthesis of the Antitumor Agent Sarkomycin". . p. 752 - 754. Retrieved 1980.
• 4、 Toki. "-". . p. 333,334. Retrieved 1958.
• 5、 Marx,Minaskanian. "". . p. 4175. Retrieved 1979.
• 6、 Westmeier, Johannes,Kress, Steffen,Pfaff, Christopher,Von Zezschwitz, Paultheo. "Total synthesis of (R)-sarkomycin via asymmetric rhodium-catalyzed conjugate addition". . p. 10718 - 10723. Retrieved 2013/11/19.