(S)-Glycidol

Base Information

• Chemical Name: (S)-Glycidol
• CAS No.: 60456-23-7
• Molecular Formula: C3H6O2
• Molecular Weight: 74.0794
• Hs Code.: 29109000
• DSSTox Substance ID: DTXSID101318083
• Nikkaji Number: J425.696D
• Wikidata: Q27117947
• Metabolomics Workbench ID: 55966
• Mol file: 60456-23-7.mol

Synonyms:(S)-Glycidol;60456-23-7;(S)-(-)-Glycidol;(S)-Oxiran-2-ylmethanol;(S)-Oxiranemethanol;[(2S)-oxiran-2-yl]methanol;(S)-(-)-2,3-Epoxy-1-propanol;Oxiranemethanol, (2S)-;(2S)-oxiran-2-ylmethanol;S-Glycidol;MFCD00074874;2-Oxiranylmethanol #;(s)-(+)-glycidol;(S)-(-)-Oxirane-2-methanol;(-)-Glycidol;(s)-(+)glycidol;(2S)-Oxiranemethanol;(s)-(+) glycidol;(S)-1-oxiranylmethanol;(2S)-2-oxiranylmethanol;(S)-oxiran-2-yl methanol;[(2S)-2-oxiranyl]methanol;CHEBI:38690;DTXSID101318083;(S)-(-)-2-(Hydroxymethyl)oxirane;AKOS005259333;AKOS015892558;AC-7041;(S)-(-)-1-Hydroxy-2,3-epoxypropane;AS-11775;AM20100474;CS-0001461;G0364;EN300-80399;H11320;A832734;A934001;Q27117947;Z1222330633;(S)-(-)-Glycidol, 97%, optical purity ee: 98% (GLC)

Chemical Property of (S)-Glycidol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Melting Point: 72-73 °C
• Refractive Index: n20/D 1.433(lit.)
• Boiling Point: 162.4 °C at 760 mmHg
• PKA: 14.62±0.10(Predicted)
• Flash Point: 81.1 °C
• PSA: 32.76000
• Density: 1.116 g/mL at 20 °C(lit.)
• LogP: -0.62250
• Storage Temp.: −20°C
• Solubility.: Soluble in chloroform, DMSO and methanol.
• 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

(S)-(-)-Glycidol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 45-60-21/22-23-36/37/38-68-41-37/38
• Safety Statements: 53-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(O1)CO
• Isomeric SMILES: C1[C@@H](O1)CO
• General Description: (S)-Oxiranemethanol, also known as (S)-glycidol, is a chiral epoxide derivative that serves as a key intermediate in the asymmetric synthesis of biologically active ether-linked phospholipids. Its enantiomeric purity is crucial for achieving high regio- and stereospecificity in nucleophilic ring-opening reactions, such as those mediated by boron trifluoride, to produce cytotoxic compounds with potential antitumor applications. The (S)-enantiomer is particularly valuable for constructing enantiomerically pure glycerophospholipid analogs, which are studied for their mechanism of action and tumor-targeting properties.

Technology Process of (S)-Glycidol

There total 25 articles about (S)-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: 92.0%

(R)-oxiran-2-ylmethyl 3,5-dinitrobenzoate (1613271-06-9) → (S)-oxiranemethanol (60456-23-7)

Guidance literature:

With methanol; for 2h; Inert atmosphere; Reflux;

Reference yield: 72.0%

allyl alcohol (107-18-6) → (S)-oxiranemethanol (60456-23-7)

Guidance literature:

With L-(+)-diisopropyl tartrate; Cumene hydroperoxide; titanium(IV) isopropylate; In dichloromethane; at 0 ℃; for 48h; Product distribution / selectivity; Molecular sieve;

Reference yield: 72.0%

(S)-3-chloropropan-1,2-diol (60827-45-4) → (S)-oxiranemethanol (60456-23-7)

Guidance literature:

With potassium carbonate; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/acs.orglett.5b02906

upstream raw materials:

1-bromo-2,3-propanediol

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

phenylacetate of 2,3-epoxypropan-1-ol

oxiranyl-methanol

Downstream raw materials:

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

tert-butyldimethylsilyl (S)-glycidyl ether

(4S)-3-benzyl-4-hydroxymethyl-oxazolidin-2-one

Benzyl-carbamic acid (S)-3-benzyl-2-oxo-oxazolidin-4-ylmethyl ester

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.

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