(2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

Base Information

• Chemical Name: (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride
• CAS No.: 859-18-7
• Molecular Formula: C18H34N2O6S^.HCl
• Molecular Weight: 443.005
• Hs Code.: 29419000
• European Community (EC) Number: 212-726-7,963-171-9
• NCI Thesaurus Code: C66013
• RXCUI: 82036
• Mol file: 859-18-7.mol

Synonyms:Epilincomycin;Hemihydrate Lincomycin Monohydrochloride;Lincocin;Lincolnensin;Lincomycin;Lincomycin A;Lincomycin Hydrochloride;Lincomycin Monohydrochloride;Lincomycin Monohydrochloride, (2S-cis)-Isomer;Lincomycin Monohydrochloride, (L-threo)-Isomer;Lincomycin Monohydrochloride, Hemihydrate;Lincomycin, (2S-cis)-Isomer;Lincomycin, (L-threo)-Isomer

Chemical Property of (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 1.85E-19mmHg at 25°C
• Melting Point: 156-158 °C
• Boiling Point: 646.8 °C at 760 mmHg
• Flash Point: 345 °C
• PSA: 147.79000
• Density: ==
• LogP: 0.27380
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 442.1904357
• Heavy Atom Count: 28
• Complexity: 499

Purity/Quality:

98%min ^*data from raw suppliers

Lincomycin hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O.Cl
• Isomeric SMILES: CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H](C([C@H]([C@H](O2)SC)O)O)O)[C@@H](C)O.Cl
• Uses: An antibiotic produced by Streptomyces lincolnensis. Lincomycin is a lincosamide antibiotic that forms cross-links within the peptidyl transferase loop region of the 23S rRNA. Inhibits bacterial protein synthesis. Antibacterial. Lincomycin hydrochloride is a salt of lincomycin formed at the basic N-methylproline. The hydrochloride salt is the preferred formulation for pharmaceutical use. Lincomycin hydrochloride is a broad spectrum antibiotic with activity against anaerobic bacteria and protozoans. Lincomycin acts by binding to the 23S ribosomal subunit, blocking protein synthesis. Lincomycin has been extensively studied with over 7,000 literature citations.
• Therapeutic Function: Antibacterial
• Clinical Use: Lincomycin is used for the treatment of infections causedby Gram-positive organisms, notably staphylococci, β-hemolyticstreptococci, and pneumococci. It is absorbed moderatelywell orally and distributed widely in the tissues.Effective concentrations are achieved in bone for the treatmentof staphylococcal osteomyelitis but not in the cerebrospinalfluid for the treatment of meningitis. At one time,lincomycin was considered a nontoxic compound, with alow incidence of allergy (rash) and occasional GI complaints(nausea, vomiting, and diarrhea) as the only adverseeffects. Recent reports of severe diarrhea and the developmentof pseudomembranous colitis in patients treated withlincomycin (or clindamycin), however, have necessitatedreappraisal of the role of these antibiotics in therapy. In anyevent, clindamycin is superior to lincomycin for thetreatment of most infections for which these antibiotics areindicated.Lincomycin hydrochloride occurs as the monohydrate, awhite, crystalline solid that is stable in the dry state. It isreadily soluble in water and alcohol, and its aqueous solutionsare stable at room temperature. It is degraded slowlyin acid solutions but is absorbed well from the GI tract.Lincomycin diffuses well into peritoneal and pleural fluidsand into bone. It is excreted in the urine and the bile. It isavailable in capsule form for oral administration and inampules and vials for parenteral administration.

Technology Process of (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride

There total 1 articles about (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide hydrochloride 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:

→ lincomycin hydrochloride (859-18-7)

Guidance literature:

Reference yield: 88.0%

lincomycin hydrochloride (859-18-7) → Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside (14810-93-6)

Guidance literature:

With water; at 100 ℃; for 72h; Inert atmosphere;

DOI:10.1021/jacs.1c03536

Reference yield:

lincomycin hydrochloride (859-18-7) → clindamycin phosphate (24729-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosgene / chloroform; N,N-dimethyl-formamide / 2 h / 5 - 71 °C / Large scale

1.2: 10 °C / Alkaline conditions; Large scale

2.1: toluene-4-sulfonic acid / acetone / 6 h / 35 °C / Large scale

3.1: triethylamine; trichlorophosphate; 1H-imidazole / acetone / 4 h / 22 °C / Large scale

3.2: 30 °C / Large scale

With 1H-imidazole; phosgene; toluene-4-sulfonic acid; triethylamine; trichlorophosphate; In chloroform; N,N-dimethyl-formamide; acetone;

Downstream raw materials:

Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside

clindamycin phosphate

clindamycin

C₂₁H₃₇ClN₂O₅S

Refernces