(2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol
• CAS No.: 22965-79-3
• Molecular Formula: C9H18ClNO4S
• Molecular Weight: 271.765
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID90704848
• Wikidata: Q82637428
• Mol file: 22965-79-3.mol

Synonyms:22965-79-3;(2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol;(2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-methylsulfanyloxane-3,4,5-triol;(2R,3R,4S,5R,6R)-2-((1S,2S)-1-Amino-2-chloropropyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triol;Methyl 7-Chloro-7-deoxy-1-thiolincosaminide;Methyl 6-amino-7-chloro-6,7,8-trideoxy-1-thio-L-threo-alfa-D-galactooctopyranoside;(2R,3R,4S,5R,6R)-2-((1S,2S)-1-amino-2-chloropropyl)-tetrahydro-6-(methylthio)-2H-pyran-3,4,5-triol;SCHEMBL14194007;DTXSID90704848;TVVQUVMUAMNLLX-WCFBUKAXSA-N;AKOS022168246;SS-4744;BP-11606;CS-0449822

Chemical Property of (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol

Chemical Property:

• PSA: 121.24000
• LogP: -0.18810
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 271.0645069
• Heavy Atom Count: 16
• Complexity: 236

Purity/Quality:

95% ^*data from raw suppliers

Methyl 7-Chloro-7-deoxy-1-thiolincosaminide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C1C(C(C(C(O1)SC)O)O)O)N)Cl
• Isomeric SMILES: C[C@@H]([C@H]([C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)SC)O)O)O)N)Cl
• Uses: Methyl 7-Chloro-7-deoxy-1-thiolincosaminid is an Intermediate in the preparation of lincomycin derived antibiotics. Intermediate in the preparation of lincomycin derived antibiotics.

Technology Process of (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol

There total 7 articles about (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol 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: 81.0%

C11H17ClF3NO5S → methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside (22965-79-3)

Guidance literature:

With sodium hydroxide; In methanol; water; at 23 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jacs.1c03529

Reference yield: 31.0%

methyl α-thiolincosaminide → methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside (22965-79-3)

Guidance literature:

With tetrachloromethane; triphenylphosphine; In acetonitrile; for 3h; Reflux;

Reference yield:

lincomycin hydrochloride (859-18-7) → methyl 6-amino-7(S)-chloro-6,7,8-trideoxy-1-thio-L-threo-α-D-galacto-octopyranoside (22965-79-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: amerlyst A-26 hydroxide form / water / 96 h / Reflux; Inert atmosphere

2.1: tributyl-amine / methanol / 4 h / 23 °C / Inert atmosphere

3.1: N-(chloromethylene)-piperidinium chloride / 1,2-dichloro-ethane / 21 h / 0 - 65 °C / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

4.1: sodium hydroxide / water; methanol / 18 h / 23 °C / Inert atmosphere

With tributyl-amine; N-(chloromethylene)-piperidinium chloride; sodium hydroxide; In methanol; water; 1,2-dichloro-ethane;

DOI:10.1021/jacs.1c03529

upstream raw materials:

lincomycin hydrochloride

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

N-trifluoroacetyl-methylthio-lincosamine

Downstream raw materials:

4-ethyl-2-pyridinecarboxamide of methyl (7S)-7-chloro-7-deoxythiolincosamide

(S)-2-[(1S,2S)-2-Chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propylcarbamoyl]-azetidine-1-carboxylic acid benzyl ester

Pirlimycin

Refernces

• 1、 -. "ALLOSTERIC MODULATORS OF 5-HYDROXYTRYPTAMINE 2C RECEPTOR (5-HT2CR)". Paragraph 000110. . Retrieved 2013/06/27.