cis-3-Methyloxiranemethanol

Base Information

• Chemical Name: cis-3-Methyloxiranemethanol
• CAS No.: 26097-34-7
• Molecular Formula: C₄H₈O₂
• Molecular Weight: 88.1063
• DSSTox Substance ID: DTXSID00460403
• Nikkaji Number: J3.498.823D
• Wikidata: Q82284441
• Mol file: 26097-34-7.mol

Synonyms:26097-34-7;cis-3-methyloxiranemethanol;CTK0I6362;DTXSID00460403;AKOS006370940

Chemical Property of cis-3-Methyloxiranemethanol

Chemical Property:

• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 53.5

Purity/Quality:

(2S,3R)-2,3-EPOXY-1-BUTANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(O1)CO
• Isomeric SMILES: C[C@@H]1[C@@H](O1)CO

Technology Process of cis-3-Methyloxiranemethanol

There total 47 articles about cis-3-Methyloxiranemethanol 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: 100.0%

(E)-but-2-enol (504-61-0,542-72-3) → 2,3-epoxybutan-1-ol (872-38-8,26097-34-7)

Guidance literature:

With tetrabutylphosphonium peroxotantalate; dihydrogen peroxide; In water; at 0 ℃; for 3.5h; chemoselective reaction; Schlenk technique;

DOI:10.1002/chem.201605661

Reference yield: 95.9%

(E/Z)-2-buten-1-ol (6117-91-5,542-72-3) → 2,3-epoxybutan-1-ol (872-38-8,26097-34-7)

Guidance literature:

With C₁₆H₃₆N⁽¹⁺⁾*H₂NbO₅^(1-); dihydrogen peroxide; In water; at 0 ℃; for 6h; chemoselective reaction;

DOI:10.1021/acscatal.6b00786

Reference yield: 84.0%

(E/Z)-2-buten-1-ol (6117-91-5,542-72-3) → (2R/3R)/(2S,3S)-2,3-epoxy-butanol (55058-23-6,26097-34-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/chem.201405317

upstream raw materials:

(E/Z)-2-buten-1-ol

epoxybutene

(E)-but-2-enol

cis-2-buten-1-ol

Downstream raw materials:

(2S,3S)-2,3-epoxy-1-butanol

((2R,3R)-3-methyloxiran-2-yl)methanol

(2R,3R)-3-(4-Methoxy-benzylamino)-butane-1,2-diol

(2R,3S)-2-(4-Methoxy-benzylamino)-butane-1,3-diol

Refernces

• 1、 Rossiter,Katsuki,Sharpless. "Asymmetric epoxidation provides shortest routes to four chiral epoxy alcohols which are key intermediates in syntheses of methymycin, erythromycin, leukotriene C-1, and disparlure". . p. 464 - 465. Retrieved 1981.
• 2、 Alickmann, Dirk,Froehlich, Roland,Wuerthwein, Ernst-Ulrich. "Base-Induced Heterochiral Dimerization of an Oxiranyl Carbaldimine: Stereoselective Synthesis of a Highly Functionalized Aziridine". . p. 1527 - 1530. Retrieved 2001.
• 3、 Zhi-min, Wang,Wei-shan, Zhou,Guo-giang, Lin. "EFFECT OF METAL HYDRIDE AND SILICA GEL ON THE SHARPLESS ASYMMETRIC EPOXIDATION". . p. 6221 - 6224. Retrieved 1985.
• 4、 Fox, Stephen J.,Gourdain, Stephanie,Coulthurst, Anton,Fox, Clare,Kuprov, Ilya,Essex, Jonathan W.,Skylaris, Chris-Kriton,Linclau, Bruno. "A computational study of vicinal fluorination in 2,3- Difluorobutane: Implications for conformational control in alkane chains". . p. 1682 - 1691. Retrieved 2015.
• 5、 Sels, Bert F.,De Vos, Dirk E.,Jacobs, Pierre A.. "Selective epoxidations involving anionic peroxotungsten compounds generated in situ on layered double hydroxides with various polarities". . p. 8557 - 8560. Retrieved 1996.
• 6、 Kumar, S. Naveen,Pavan Kumar, C. H. N. S. Sai,Srihari,Kancharla, Sravani,Srinivas, Kolupula,Shrivastava, Shweta,Naidu,Jayathirtha Rao. "First total synthesis of fuzanins C, D and their analogues as anticancer agents". . p. 8365 - 8375. Retrieved 2014.
• 7、 Corsano,Piancatelli. "-". . p. 1106. Retrieved 1971.
• 8、 Ding, Bingjie,Hou, Zhenshan,Li, Difan,Ma, Wenbao,Yao, Yefeng,Zhang, Ran,Zheng, Anna,Zhou, Qingqing. "Olefin epoxidation with ionic liquid catalysts formed by supramolecular interactions". . . Retrieved 2020/12/29.
• 9、 Zhang, Zhi,Li, Yunfeng,Zhang, Rentao,Yu, Xiaoming. "Total Synthesis of Geldanamycin". . p. 15063 - 15075. Retrieved 2021/11/01.