Dihydroxybusulfan

Base Information

• Chemical Name: Dihydroxybusulfan
• CAS No.: 1947-62-2
• Molecular Formula: C6H14 O8 S2
• Molecular Weight: 278.304
• Hs Code.: 2905499000
• NSC Number: 260698,39069,39068
• Wikidata: Q7838652
• ChEMBL ID: CHEMBL2358556
• Mol file: 1947-62-2.mol

Synonyms:Dimesyl-meso-erythritol;Erythritol, 1,4-dimethanesulfonate;Erythritol, dimesyl-, meso-;Dihydroxymyleran;Dihydroxybusulfan;1,4-Di(methanesulfonate)erythritol;NSC 94160;L-Threityl dimesylate;Erythritol, 1,4-bis(methanesulfonate);Threitol-1,4-bismethanesulfonate, meso-;CB 40069;1,4-Bis(methanesulfonyloxy)-2,3-butanediol;1,4-Bis(methylsulfonyloxy)threitol;Threitol 1,4-bis(methanesulfonate);ERYTHRITOL, 1,4-DIMETHANESULFONATE, (meso)-;NCGC00181153-01;1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate, (R*,S*)-;1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate, (R-(R*,S*))-;C6H14O8S2;1,4-Bis mesyl ester of D-threitol;CB 40065;Treosulfan [BAN:INN];NSC 39069;Treosulphan;DHB;DTXSID0026173;Treosulfa;C6-H14-O8-S2;21106-06-9;(2S,4-bismethanesulfonate;D04YPN;SCHEMBL8142;NCIOpen2_006538;Threitol,4-dimethanesulfonate;treosulfan, (R*,S*)-isomer;[(2S,3S)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate;DTXCID106173;GTPL8281;1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate, (R-(R*,R*))- (9CI);CHEMBL2358556;(2,3-dihydroxy-4-methylsulfonyloxybutyl) methanesulfonate;1,4-DimethanesulfonateL-Threitol;Threitol, 1,4-dimethanesulfonate;Threitol,4-dimethanesulfonate, L-;BCP31509;D-Threitol,4-bis(methanesulfonate);L-Threitol,4-bis(methanesulfonate);NSC39068;NSC39069;Tox21_112757;NSC-39068;NSC260698;NSC 260698;NSC-260698;L-Threitol-1, 4-bis(methanesulfonate);Threitol,4-dimethanesulfonate, L-(+)-;1,4-DimethanesulfonateL-(+ )-Threitol;L-Threitol, 1, 4-bis(methanesulfonate);1,4-Dimethanesulfonate(2S,3S)-Threitol;CAS-299-75-2;LS-64629;Threitol,4-dimethanesulfonate, (2S,3S)-;E83713;2,3-dihydroxybutane-1,4-diyl dimethanesulfonate;Q7838652;1,2,3,4-Butanetetrol, 1,4-dimethanesulfonate, (R*,R*)-;1,3,4-Butanetetrol, 1,4-dimethanesulfonate, (R*,R*)-;2,3-dihydroxy-4-(methanesulfonyloxy)butyl methanesulfonate;NSC-39069;Ovastat;1,3,4-Butanetetrol, 1,4-dimethanesulfonate, [R-(R*,R*)]-;1,3,4-Butanetetrol, 1,4-dimethanesulfonate, [S-(R*,R*)]-

Chemical Property of Dihydroxybusulfan

Chemical Property:

• Vapor Pressure: 2.86E-17mmHg at 25°C
• Melting Point: 102-103 °C
• Refractive Index: 1.517
• 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:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CS(=O)(=O)OCC(C(COS(=O)(=O)C)O)O
• Recent NIPH Clinical Trials: Development of treosulfan-based conditioning regimen for congenital metabolic diseases; Phase I study

Technology Process of Dihydroxybusulfan

There total 13 articles about Dihydroxybusulfan 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: 81.0%

2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol (109281-59-6) → treosulfan (1947-62-2,5380-21-2)

Guidance literature:

With methanesulfonic acid; In ethanol; water;

DOI:10.1002/chir.22814

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:

L-4,5-Bismethylsulfonyloxymethyl-1,3,2-dioxathiolane 2-Oxide

(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

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.