(+/-)-2-Hydroxy-3-buten-1-yl tosylate

Base Information

• Chemical Name: (+/-)-2-Hydroxy-3-buten-1-yl tosylate
• CAS No.: 138332-13-5
• Molecular Formula: C11H14O4S
• Molecular Weight: 242.296
• DSSTox Substance ID: DTXSID40393620
• Nikkaji Number: J2.282.452J
• Mol file: 138332-13-5.mol

Synonyms:(+/-)-2-Hydroxy-3-buten-1-yl tosylate;138332-13-5;2-hydroxybut-3-enyl 4-methylbenzenesulfonate;SCHEMBL4446042;1-Tosyloxy-2-hydroxy-3-butene;DTXSID40393620;YQSCDBZHHLIPOI-UHFFFAOYSA-N;FT-0655381;FT-0770807;p-Toluenesulfonic acid 2-hydroxy-3-butenyl ester;A807359;toluene-4-sulfonic acid 2-hydroxy-but-3-enyl ester;(R)-2-Hydroxybut-3-en-1-yl 4-methylbenzenesulfonate;1-[(4-METHYLBENZENESULFONYL)OXY]BUT-3-EN-2-OL

Chemical Property of (+/-)-2-Hydroxy-3-buten-1-yl tosylate

Chemical Property:

• PSA: 71.98000
• LogP: 2.32800
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 242.06128010
• Heavy Atom Count: 16
• Complexity: 309

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(C=C)O

Technology Process of (+/-)-2-Hydroxy-3-buten-1-yl tosylate

There total 5 articles about (+/-)-2-Hydroxy-3-buten-1-yl tosylate 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: 97.0%

3,4-butenediol (497-06-3,86161-40-2) + p-toluenesulfonyl chloride (98-59-9) → 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate (138332-13-5)

Guidance literature:

With di(n-butyl)tin oxide; triethylamine; In dichloromethane; water; at 20 ℃;

DOI:10.1021/tx060016o

Reference yield: 68.0%

3,4-butenediol (497-06-3,86161-40-2) + toluene-4-sulfonic acid (104-15-4) → 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate (138332-13-5)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1002/(SICI)1099-0690(199907)1999:7<1671::AID-EJOC1671>3.0.CO;2-Z

Reference yield:

→ 2-hydroxy-3-butenyl-4-methyl-1-benzenesulfonate (138332-13-5) + Dimethyl succinate (106-65-0)

Guidance literature:

upstream raw materials:

3,4-butenediol

p-toluenesulfonyl chloride

toluene-4-sulfonic acid

dmap

Downstream raw materials:

(R)-1-tosyloxy-2-acetyloxy-3-butene

(S)-2-hydroxy-3-buten-1-yl p-tosylate

2-hydroxy-(2R)-3-butenyl-4-methyl-1-benzenesulfonate

(±)-2-acetoxybut-3-enyl tosylate

Refernces

• 1、 Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa. "Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent". supporting information. p. 3981 - 3988. Retrieved 2018/06/15.
• 2、 Guillaume, Michel,Lang, Yolande. "Further improvements of the dibutyl tin oxide-catalyzed regioselective diol tosylation". experimental part. p. 579 - 582. Retrieved 2010/04/02.