(2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran

Base Information

• Chemical Name: (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran
• CAS No.: 220623-67-6
• Molecular Formula: C₁₁H₁₃FO₃
• Molecular Weight: 212.221
• DSSTox Substance ID: DTXSID00445376
• Mol file: 220623-67-6.mol

Synonyms:(2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran;220623-67-6;SCHEMBL7016028;DTXSID00445376;IVKSQNHLIMRJAC-VUWPPUDQSA-N;(2S)-(4-fluorophenoxymethyl)5-hydroxytetrahydrofuran

Chemical Property of (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 212.08487243
• Heavy Atom Count: 15
• Complexity: 192

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC(OC1COC2=CC=C(C=C2)F)O
• Isomeric SMILES: C1CC(O[C@@H]1COC2=CC=C(C=C2)F)O

Technology Process of (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran

There total 5 articles about (2S)-(4-fluorophenoxymethyl)-5-hydroxytetrahydrofuran 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: 100.0%

(5S)-5-(4-fluorophenoxymethyl)-γ-butyrolactone (175212-40-5) → (2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran (220623-67-6)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃;

DOI:10.1080/00397910008087245

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran (220623-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / PPh₃; DIAD / tetrahydrofuran / 3 h

2: 100 percent / DIBAL-H / toluene / -78 °C

With di-isopropyl azodicarboxylate; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1039/b316858a

Reference yield:

4-Fluorophenol (371-41-5) → (2RS,5S)-5-(4-fluorophenoxymethyl)-2-hydroxytetrahydrofuran (220623-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / PPh₃; DIAD / tetrahydrofuran / 3 h

2: 100 percent / DIBAL-H / toluene / -78 °C

With di-isopropyl azodicarboxylate; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1039/b316858a

upstream raw materials:

(5S)-5-(4-fluorophenoxymethyl)-γ-butyrolactone

4-Fluorophenol

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

L-glutamic acid

Downstream raw materials:

(5S)-5-(4-fluorophenoxymethyl)-2-(tert-butyldimethylsiloxy)tetrahydrofuran

(2RS,5S)-5-(4-fluorophenoxymethyl)-2-(but-3-yne-1-oxy)tetrahydrofuran