Oxiraneethanol, (2R)-

Base Information

• Chemical Name: Oxiraneethanol, (2R)-
• CAS No.: 76282-48-9
• Molecular Formula: C4H8O2
• Molecular Weight: 88.1063
• DSSTox Substance ID: DTXSID70473944
• Nikkaji Number: J1.029.224G
• Wikidata: Q82303645
• Mol file: 76282-48-9.mol

Synonyms:Oxiraneethanol, (2R)-;76282-48-9;(r)-2-(oxiran-2-yl)ethanol;(R)-2-(Oxiran-2-yl)ethan-1-ol;2-[(2R)-Oxiran-2-yl]ethan-1-ol;R-3,4-Epoxy-1-butanol;(r)-3,4-epoxy-1-butanol;(A+/-)-2-Oxiranyl-ethanol;2-[(2R)-oxiran-2-yl]ethanol;DTXSID70473944;AKOS006344917;CS-0057154;D72936;A903938

Chemical Property of Oxiraneethanol, (2R)-

Chemical Property:

• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.052429494
• Heavy Atom Count: 6
• Complexity: 44.8

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CCO
• Isomeric SMILES: C1[C@H](O1)CCO

Technology Process of Oxiraneethanol, (2R)-

There total 26 articles about Oxiraneethanol, (2R)- 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: 94.0%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) → (R)-2-(oxiran-2-yl)ethan-1-ol (76282-48-9)

Guidance literature:

L-Aspartic acid; With sulfuric acid; sodium bromide; sodium nitrite; In water; at 0 ℃; for 2h;

With dimethylsulfide borane complex; In tetrahydrofuran; at -20 - 23 ℃; for 13h;

With caesium carbonate; In dichloromethane; at 23 ℃; for 12h;

DOI:10.1016/j.bmcl.2015.09.021

Reference yield: 92.4%

(S)-1,2,4-butanetriol 1,4-diacetate 2-methanesulfonate (76282-47-8) → (R)-2-(oxiran-2-yl)ethan-1-ol (76282-48-9)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)91498-X

Reference yield: 92.0%

C6H10O3 (1092554-94-3) → (S)-2-(oxiran-2-yl)ethan-1-ol (19098-31-8,76282-48-9,84985-50-2,95404-59-4)

Guidance literature:

With lipase from Rhizomucor miehei, expressed in Aspergillus oryzae; for 14h; pH=7.5; aq. phosphate buffer;

DOI:10.1016/j.tetlet.2008.08.097

upstream raw materials:

(2R)-2-(2-benzyloxyethyl)oxirane

(S)-1,2,4-butanetriol 1,4-diacetate 2-methanesulfonate

(R)-2-Bromo-1,4-butanediol 1,4-diacetate

5-(d)-menthyloxy-4-phenylthiobutyrolactone

Downstream raw materials:

(R)-2-(2-(tert-butyldimethylsilyloxy)ethyl)oxirane

(2-((S)-oxiran-2-yl)ethoxy)(tert-butyl)dimethylsilane

(R)-<2<(Methanesulfonyl)oxy>ethyl>oxirane

Refernces

• 1、 Fernandes, Rodney A.,Kumar, Praveen,Saini, Deepak. "Stereoselective total synthesis of obolactones and 7′,8′-dihydroobolactones". . p. 18976 - 18982. Retrieved 2021/10/29.
• 2、 Cheviet, Thomas,Wein, Sharon,Bourchenin, Gabriel,Lagacherie, Manon,Périgaud, Christian,Cerdan, Rachel,Peyrottes, Suzanne. "β-Hydroxy- A nd β-Aminophosphonate Acyclonucleosides as Potent Inhibitors of Plasmodium falciparum Growth". . p. 8069 - 8087. Retrieved 2020/08/12.