3-Deoxy-3-fluoroinositol 1,4,5-trisphosphate

Base Information

• Chemical Name: 3-Deoxy-3-fluoroinositol 1,4,5-trisphosphate
• CAS No.: 144371-38-0
• Molecular Formula: C6H14 F O14 P3
• Molecular Weight: 422.088
• DSSTox Substance ID: DTXSID70162689
• Wikidata: Q83031425
• Mol file: 144371-38-0.mol

Synonyms:3-deoxy-3-fluoro-D-myo-inositol 1,4,5-trisphosphate;3-deoxy-3-fluoro-Ins(1,4,5)P3;3-deoxy-3-fluoroinositol 1,4,5-trisphosphate;3-F-InsP3;Ins(1,4,5)P(3)F

Chemical Property of 3-Deoxy-3-fluoroinositol 1,4,5-trisphosphate

Chemical Property:

• Vapor Pressure: 1.23E-34mmHg at 25°C
• Boiling Point: 862°Cat760mmHg
• PKA: 1.91±0.10(Predicted)
• Flash Point: 475.1°C
• PSA: 270.17000
• Density: 2.17g/cm³
• LogP: -2.50640
• XLogP3: -6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 421.95804427
• Heavy Atom Count: 24
• Complexity: 579

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(C(C(C(C(C1OP(=O)(O)O)OP(=O)(O)O)F)O)OP(=O)(O)O)O
• Isomeric SMILES: [C@@H]1([C@@H]([C@@H]([C@H]([C@H]([C@@H]1OP(=O)(O)O)OP(=O)(O)O)F)O)OP(=O)(O)O)O

Technology Process of 3-Deoxy-3-fluoroinositol 1,4,5-trisphosphate

There total 8 articles about 3-Deoxy-3-fluoroinositol 1,4,5-trisphosphate 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: 80.0%

Phosphoric acid dibenzyl ester (1R,2S,3R,4S,5S,6S)-2-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-5-fluoro-6-hydroxy-cyclohexyl ester (129365-67-9) → Phosphoric acid mono-((1S,2S,3S,4S,5R,6S)-3-fluoro-2,6-dihydroxy-4,5-bis-phosphonooxy-cyclohexyl) ester (144371-38-0)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethanol; at 23 ℃; for 14h;

DOI:10.1021/ja00176a055

Reference yield:

(3aS,4S,4aR,7aS,8S,8aS)-8-Fluoro-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol (129444-05-9) → Phosphoric acid mono-((1S,2S,3S,4S,5R,6S)-3-fluoro-2,6-dihydroxy-4,5-bis-phosphonooxy-cyclohexyl) ester (144371-38-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / NaH / tetrahydrofuran / 12 h / 0 - 23 °C

2: 86 percent / methanol. HCl / CH₂Cl₂ / 0.67 h / 23 °C

3: 92 percent / pyridine, 4-dimethylaminopyridine (DMAP) / 12 h / 23 °C

4: 92 percent / conc. HCl, MeOH / 6 h / 23 °C

5: 76 percent / pyridine / 22 h / 0 °C

6: 86 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / 12 h / 0 - 23 °C

7: 83 percent / K₂CO₃ / methanol / 14 h / 23 °C

8: 95 percent / NaH / dimethylformamide / 8 h / 0 °C

9: 82 percent / p-toluenesulfonic acid (p-TSA) / methanol / 14 h / 23 °C

10: 80 percent / H₂ / PtO₂ / ethanol / 14 h / 23 °C

With pyridine; hydrogenchloride; methanol; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00176a055

Reference yield:

(3aS,4S,4aR,7aS,8S,8aS)-4-Benzyloxy-8-fluoro-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole (129365-59-9) → Phosphoric acid mono-((1S,2S,3S,4S,5R,6S)-3-fluoro-2,6-dihydroxy-4,5-bis-phosphonooxy-cyclohexyl) ester (144371-38-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 86 percent / methanol. HCl / CH₂Cl₂ / 0.67 h / 23 °C

2: 92 percent / pyridine, 4-dimethylaminopyridine (DMAP) / 12 h / 23 °C

3: 92 percent / conc. HCl, MeOH / 6 h / 23 °C

4: 76 percent / pyridine / 22 h / 0 °C

5: 86 percent / pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂ / 12 h / 0 - 23 °C

6: 83 percent / K₂CO₃ / methanol / 14 h / 23 °C

7: 95 percent / NaH / dimethylformamide / 8 h / 0 °C

8: 82 percent / p-toluenesulfonic acid (p-TSA) / methanol / 14 h / 23 °C

9: 80 percent / H₂ / PtO₂ / ethanol / 14 h / 23 °C

With pyridine; hydrogenchloride; methanol; dmap; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; platinum(IV) oxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00176a055

upstream raw materials:

Phosphoric acid dibenzyl ester (1R,2S,3R,4S,5S,6S)-2-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-5-fluoro-6-hydroxy-cyclohexyl ester

(3aS,4S,4aR,7aS,8S,8aS)-8-Fluoro-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol

(3aS,4R,5S,6S,7R,7aS)-4-Benzyloxy-7-fluoro-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5,6-diol

(1S,2S,3R,4S,5S,6R)-3-Benzyloxy-5-(1-ethoxy-ethoxy)-6-fluoro-cyclohexane-1,2,4-triol