2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-
• CAS No.: 4624-52-6
• Molecular Formula: C₁₇H₂₀O₈
• Molecular Weight: 352.341
• DSSTox Substance ID: DTXSID40196779
• Nikkaji Number: J16.272H
• Wikidata: Q83069792
• Mol file: 4624-52-6.mol

Synonyms:Psilotin;4624-52-6;2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-;DTXSID40196779

Chemical Property of 2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-

Chemical Property:

• Vapor Pressure: 8.66E-18mmHg at 25°C
• Boiling Point: 650.1°Cat760mmHg
• Flash Point: 239.5°C
• PSA: 125.68000
• Density: 1.476g/cm³
• LogP: -0.59050
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 352.11581759
• Heavy Atom Count: 25
• Complexity: 487

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(=O)OC1C2=CC=C(C=C2)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1C=CC(=O)O[C@@H]1C2=CC=C(C=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• General Description: (S)-6-[4-(β-D-Glucopyranosyloxy)phenyl]-5,6-dihydro-2H-pyran-2-one, also known as psilotin, is a naturally occurring glucoside isolated from *Psilotum nudum* and *Tmesipteris tannensis*, exhibiting growth inhibitory properties. It features a dihydropyran-2-one core linked to a phenyl group substituted with a β-D-glucopyranosyl moiety. (S)-6-[4-(β-D-Glucopyranosyloxy)phenyl]-5,6-dihydro-2H-pyran-2-one's synthesis involves the aglycon psilotinin, derived from 4-(methylthiomethoxy)benzaldehyde, followed by glucosidation using protected glucose derivatives. Spectroscopic analysis confirms its (S)-configuration at the C-6 position. Psilotin's structural and synthetic details highlight its significance as a bioactive natural product.

Technology Process of 2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)-

There total 6 articles about 2H-Pyran-2-one, 6-(4-(beta-D-glucopyranosyloxy)phenyl)-5,6-dihydro-, (S)- 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:

4-formyl-1-(methylsulfenyl)methoxybenzene (41967-53-7) → Psilotin (4624-52-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH, 15 percent butyl lithium (liq.) / 1) THF, hexane, 10 min., 0 deg C, 10 min.; 2) THF, 30 min., 0 deg C

2: 38 percent / pyridine / tetrahydrofuran / 6 h / -20 °C

3: 46 percent / NaBH₄ / dimethylsulfoxide / 6 h / Ambient temperature

4: 75 percent / HgCl₂ / acetonitrile; H₂O / 6 h / 75 °C

5: 1) azodicarbonic acid diethylester, triphenylphosphane; 2) pyridinium toluene sulfonate / 1) ether, 12 h, room temp.; 2) C₂H₅OH, 18 h, room temp.

With pyridine; sodium tetrahydroborate; n-butyllithium; diethyl azodicarbonate; pyridinium p-toluenesulfonate; sodium hydride; triphenylphosphine; mercury dichloride; In tetrahydrofuran; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/jlac.198119811222

Reference yield:

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → Psilotin (4624-52-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) NaH (80 percent)/ paraffine / 1) HMPT, 1 h, room temp.; 2) 12 h, room temp.

2: 1) NaH, 15 percent butyl lithium (liq.) / 1) THF, hexane, 10 min., 0 deg C, 10 min.; 2) THF, 30 min., 0 deg C

3: 38 percent / pyridine / tetrahydrofuran / 6 h / -20 °C

4: 46 percent / NaBH₄ / dimethylsulfoxide / 6 h / Ambient temperature

5: 75 percent / HgCl₂ / acetonitrile; H₂O / 6 h / 75 °C

6: 1) azodicarbonic acid diethylester, triphenylphosphane; 2) pyridinium toluene sulfonate / 1) ether, 12 h, room temp.; 2) C₂H₅OH, 18 h, room temp.

With pyridine; sodium tetrahydroborate; n-butyllithium; paraffine; diethyl azodicarbonate; pyridinium p-toluenesulfonate; sodium hydride; triphenylphosphine; mercury dichloride; In tetrahydrofuran; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/jlac.198119811222

Reference yield:

5,6-Dihydro-4-hydroxy-6-<4-(methylthiomethoxy)phenyl>-2H-pyran-2-on (80727-06-6) → Psilotin (4624-52-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 38 percent / pyridine / tetrahydrofuran / 6 h / -20 °C

2: 46 percent / NaBH₄ / dimethylsulfoxide / 6 h / Ambient temperature

3: 75 percent / HgCl₂ / acetonitrile; H₂O / 6 h / 75 °C

4: 1) azodicarbonic acid diethylester, triphenylphosphane; 2) pyridinium toluene sulfonate / 1) ether, 12 h, room temp.; 2) C₂H₅OH, 18 h, room temp.

With pyridine; sodium tetrahydroborate; diethyl azodicarbonate; pyridinium p-toluenesulfonate; triphenylphosphine; mercury dichloride; In tetrahydrofuran; water; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/jlac.198119811222

upstream raw materials:

Psilotinin

4-formyl-1-(methylsulfenyl)methoxybenzene

4-hydroxy-benzaldehyde

5,6-Dihydro-6-<4-(methylthiomethoxy)phenyl>-2H-pyran-2-on

Refernces

Investigation of natural γ- and δ-lactones. XI. Synthesis of psilotin and 6-epipsilotin

10.1002/jlac.198119811222

The study focuses on the synthesis of psilotin (1) and its 6-epi isomer. Psilotin is a glucoside found in the shoots of Psilotum nudum and Tmesipteris tannensis, and it is of interest as a growth inhibitor. The synthesis process involves several key steps and compounds. Initially, psilotinin (2), the aglycon of psilotin, is synthesized through a series of reactions starting from 4-(methylthiomethoxy)benzaldehyde (4). This compound is condensed with the dianion of acetessigsaureester to form an intermediate, which is then converted to psilotinin by removing the 4-OH group via reduction with NaBH4 in DMSO. The glucosidation of psilotinin is achieved using 2,3,4,6-tetra-O-acetylglucose in the presence of azodicarbons?ureester and triphenylphosphane, yielding a mixture of anomers that are separated chromatographically. The study also describes the synthesis of protected glucose derivatives, such as 2,3,4,6-tetra-O-(1-ethoxyethyl)-D-glucopyranose (11), to facilitate milder conditions for deprotection. The final products, including psilotin and its epimers, are characterized by various spectroscopic methods, confirming their structures and the absolute configuration at the C-6 position of psilotin as 6S.

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