(R)-Glycidol

Base Information

• Chemical Name: (R)-Glycidol
• CAS No.: 57044-25-4
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 29109000
• European Community (EC) Number: 404-660-4,629-598-7
• DSSTox Substance ID: DTXSID40904710
• Nikkaji Number: J425.695F
• Wikidata: Q27109084
• Metabolomics Workbench ID: 53646
• Mol file: 57044-25-4.mol

Synonyms:(R)-Glycidol;57044-25-4;(R)-(+)-Glycidol;(R)-Oxiran-2-ylmethanol;[(2R)-oxiran-2-yl]methanol;(R)-Oxiranemethanol;(+)-Glycidol;Oxiranemethanol, (2R)-;(R)-3-hydroxy-1,2-epoxypropane;(2R)-oxiran-2-ylmethanol;(R)-(+)-Oxirane-2-methanol;(R)-(+)-2,3-Epoxy-1-propanol;2-Oxiranylmethanol #;R(+)-glycidol;R-2,3-epoxy-1-propanol;rac-glycidol;(+) glycidol;R(+) glycidol;EC 404-660-4;(r )-(+)-glycidol;(r)-1-oxiranyl-methanol;(2R)-2-oxiranylmethanol;2,3 Epossipropan-1-Olo;CHEBI:18664;DTXSID40904710;(R)-(+)-2-(Hydroxymethyl)oxirane;AKOS016842463;AC-7042;AM81447;CS-W013757;(R)-(+)-Glycidol, analytical standard;(R)-(+)-1-Hydroxy-2,3-epoxypropane;AS-11738;G0363;EN300-80398;A831293;Q27109084;Z1222330631;(R)-(+)-Glycidol, 97%, optical purity ee: 98% (GLC)

Chemical Property of (R)-Glycidol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Refractive Index: n20/D 1.43(lit.)
• Boiling Point: 162.4 °C at 760 mmHg
• PKA: 14.62±0.10(Predicted)
• Flash Point: 81.1 °C
• PSA: 32.76000
• Density: 1.178 g/cm³
• LogP: -0.62250
• Storage Temp.: 2-8°C
• Water Solubility.: Completely miscible in water
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 74.036779430
• Heavy Atom Count: 5
• Complexity: 35.9

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-Glycidol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, E
• Hazard Codes: T,E
• Statements: 45-60-2-21/22-23-34-68-41-37/38
• Safety Statements: 53-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CO
• Isomeric SMILES: C1[C@H](O1)CO
• General Description: (R)-(+)-Glycidol is a chiral epoxide alcohol widely used as a key intermediate in asymmetric synthesis, particularly in the production of biologically active compounds such as cytotoxic ether-linked phospholipids and natural products like (+)-testudinariol A. Its enantiomeric purity and reactivity make it valuable for regio- and stereospecific transformations, as demonstrated in studies where it serves as a precursor for antitumor agents or marine-derived metabolites. The compound's versatility is highlighted by its role in forming enantiomerically pure glycerophospholipids and complex triterpenes, underscoring its importance in medicinal and synthetic chemistry.

Technology Process of (R)-Glycidol

There total 27 articles about (R)-Glycidol 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: 88.0%

(2R)-3-chloro-1,2-propanediol (57090-45-6) → (R)-oxiranemethanol (57044-25-4)

Guidance literature:

With potassium carbonate; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo981332d

Reference yield: 88.0%

(2R)-3-bromo-1,2-propanediol (14437-88-8) → (R)-oxiranemethanol (57044-25-4)

Guidance literature:

With potassium carbonate; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jo981332d

Reference yield: 45.0%

allyl alcohol (107-18-6) → (R)-oxiranemethanol (57044-25-4) + (S)-oxiranemethanol (60456-23-7)

Guidance literature:

With tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; tantalum pentaethoxide; In dichloromethane; at 0 ℃; for 48h; Product distribution / selectivity; Molecular sieve;

upstream raw materials:

(R)-3-tosyloxy-1,2-propanediol

Pentanoic acid oxiranylmethyl ester

phenylacetate of 2,3-epoxypropan-1-ol

vinyl acetate

Downstream raw materials:

4-{4-[(2S)-oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl}morpholine

(R)-3-<<4-(benzyloxy)phenyl>amino>-1,2-propanediol

(R)-3-<<4-<(3-chlorophenyl)methoxy>phenyl>amino>-1,2-propanediol

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

Refernces

Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids

10.1021/jo00280a034

The research focuses on the asymmetric synthesis of unnatural, cytotoxic ether-linked phospholipids, which are biologically active molecules with potential antitumor activity. The key step in this synthesis involves the highly regio- and stereospecific nucleophilic opening of glycidyl derivatives using boron trifluoride etherate as a catalyst, yielding enantiomeric excess of over 94%. The study successfully developed a short and efficient method to produce enantiomerically pure 1-O-alkyl-2-O-methyl-sn-glycero-3-phosphocholine (5a) and 3-O-alkyl-2-O-methyl-1-sn-glycero-phosphocholine (5b) from optically active glycidyl derivatives, which can be used to study the mechanism of cytotoxic activity and tumor specificity of these anti-neoplastic agents. The chemicals used in the process include p-toluenesulfonate and tert-butyldiphenylsilyl ether derivatives of (R)- and (S)-glycidol, 1-hexadecanol, and various reagents for the subsequent steps of the synthesis, such as methyl triflate, potassium superoxide, and 2-chloro-2-oxo-1,3,2-dioxaphospholane.

Synthesis of (+)-testudinariol A, a triterpene metabolite of the marine mollusc Pleurobrancus testudinarius

10.1016/S0040-4039(00)02179-1

The research focuses on the synthesis of (+)-testudinariol A, a triterpene metabolite derived from the marine mollusc Pleurobrancus testudinarius, known for its ichthyotoxic properties. The purpose of the study was to achieve a stereoselective synthesis of (+)-testudinariol A, starting from (R)-glycidol. The researchers successfully synthesized the compound through a series of chemical reactions, including selective protection of hydroxy groups, oxidative cleavage, Horner–Wadsworth–Emmons reaction, Michael-type cyclization, and ene reaction, among others. The conclusion of the research was the first successful synthesis of (+)-testudinariol A, with an overall yield of 4.4% based on the starting material in 19 steps, and the synthetic product's physical and spectral data were in good agreement with those reported for the naturally occurring compound. The study also mentioned ongoing work to optimize each step and the synthesis of testudinariol B (2).