Treosulfan

Base Information

• Chemical Name: Treosulfan
• CAS No.: 299-75-2
• Deprecated CAS: 14461-01-9,5592-88-1,27863-55-4
• Molecular Formula: C₆H₁₄O₈S₂
• Molecular Weight: 278.304
• European Community (EC) Number: 206-081-0
• UNII: CO61ER3EPI
• DSSTox Substance ID: DTXSID0026173
• Nikkaji Number: J8.627D
• Wikipedia: Treosulfan
• NCI Thesaurus Code: C1257
• Metabolomics Workbench ID: 152795
• ChEMBL ID: CHEMBL455186
• Mol file: 299-75-2.mol

Synonyms:L-dihydroxybusulfan;L-threitol-1,4-bismethanesulfonate;NSC 39069;treosulfan;treosulfan, ((R*,R*)-(+-))-isomer;treosulfan, (R*,R*)-isomer;treosulfan, (R*,S*)-isomer;treosulfan, (R-(R*,R*))-isomer

Chemical Property of Treosulfan

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 76-78 °C
• Refractive Index: 1.518
• Boiling Point: 607°Cat760mmHg
• PKA: 12.36±0.20(Predicted)
• Flash Point: 320.9°C
• PSA: 143.96000
• Density: 1.562g/cm³
• LogP: -0.17780
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 278.01300975
• Heavy Atom Count: 16
• Complexity: 345

Purity/Quality:

99%, ^*data from raw suppliers

Treosulfan ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OCC(C(COS(=O)(=O)C)O)O
• Isomeric SMILES: CS(=O)(=O)OC[C@@H]([C@H](COS(=O)(=O)C)O)O
• Recent ClinicalTrials: Donor Stem Cell Transplant With Treosulfan, Fludarabine, and Thiotepa in Treating Patients With Non-malignant Disorders
• Recent EU Clinical Trials: Prospective Phase II study on Safety and Efficacy of Fludarabine plus Treosulfan (14g) (FT14) conditioning regimen for allogeneic Stem Cell Transplantation (allo-SCT) in Acute Myeloid Leukemia (AML) patients (=40 <65years)
• Recent NIPH Clinical Trials: Development of treosulfan-based conditioning regimen for congenital metabolic diseases; Phase I study
• Clinical Use: Alkylating agent for ovarian cancer
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Treosulfan

There total 10 articles about Treosulfan 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: 92.0%

(4S,5S)-2-phenyl-4,5-di(methanesulphonyloxymethyl)-1,3-dioxolan (94730-27-5) → treosulfan (299-74-1,1947-62-2,13308-13-9,17088-46-9,21106-06-9,299-75-2,5380-21-2)

Guidance literature:

With phosphomolybdic acid; silica gel; In acetonitrile; at 20 ℃; for 0.75h; chemoselective reaction;

DOI:10.1002/ejoc.200800963

Reference yield: 85.0%

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) dimethanesulfonate (4248-74-2) → treosulfan (299-74-1,1947-62-2,13308-13-9,17088-46-9,21106-06-9,299-75-2,5380-21-2)

Guidance literature:

With methanesulfonic acid; In ethanol; water;

DOI:10.1002/chir.22814

Reference yield:

[(4S,5S)-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-diyl]bis(methylene)dimethanesulfonate → treosulfan (299-74-1,1947-62-2,13308-13-9,17088-46-9,21106-06-9,299-75-2,5380-21-2)

Guidance literature:

With hydrogenchloride; In methanol; water; at 15 - 25 ℃; Temperature;

upstream raw materials:

((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene) dimethanesulfonate

methanesulfonic acid

(S,S)-diepoxybutane

silver methanesulfonate

Downstream raw materials:

(S,S)-diepoxybutane

(R,R)-butane-1,2:3,4-bisoxide

((2S,3S)-1,4-dioxaspiro[4.5]decane-2,3-diyl)bis(methylene) dimethanesulfonate

Di-2,3-O-carbethoxy-L-threitol-1,4-bismethanesulfonate

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF TREOSULFAN". Page/Page column 22. . Retrieved 2019/03/17.
• 2、 Kumar, Ponminor Senthil,Kumar, Gaddale Devanna Kishore,Baskaran, Sundarababu. "Truly catalytic and chemoselective cleavage of benzylidene acetal with phosphomolybdic acid supported on silica gel". supporting information; scheme or table. p. 6063 - 6067. Retrieved 2009/05/27.