(4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
• CAS No.: 166275-25-8
• Molecular Formula: C₅H₆F₂O₄
• Molecular Weight: 168.097
• DSSTox Substance ID: DTXSID50445301
• Wikidata: Q82263667
• Mol file: 166275-25-8.mol

Synonyms:166275-25-8;(4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one;(4S,5S)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-one;L-erythro-Pentonic acid, 2-deoxy-2,2-difluoro-,gamma-lactone;DTXSID50445301;FBXJTMLCLDWDQO-HRFVKAFMSA-N;CS-0447792

Chemical Property of (4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Chemical Property:

• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 168.02341499
• Heavy Atom Count: 11
• Complexity: 181

Purity/Quality:

98%min ^*data from raw suppliers

(4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(=O)O1)(F)F)O)O
• Isomeric SMILES: C([C@H]1[C@@H](C(C(=O)O1)(F)F)O)O
• Uses: 2-Deoxy-2,2-difluoro -L-threo-pentonic Acid γ-lactone is used in the synthesis of anti-HIV Deoxydifluoro Nucleosides.

Technology Process of (4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

There total 1 articles about (4S,5S)-3,3-Difluoro-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 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:

(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester (166376-98-3,166376-97-2) → (4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (166275-25-8)

Guidance literature:

With Dowex-50 (H⁺) resin; water; In methanol; for 120h;

DOI:10.1021/jm970275y

Reference yield:

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (166275-25-8) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α,β-L-erythro-pentofuranos-1-yl)-5-iodouracil

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 36 h / Ambient temperature

2: 33 percent / Li(t-BuO)3AlH / tetrahydrofuran / 0.67 h / -50 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: TMSOTf / 1,2-dichloro-ethane / 10 h / 90 - 100 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm970275y

Reference yield:

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (166275-25-8) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)uracil (197452-19-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / CH₂Cl₂ / 36 h / Ambient temperature

2: 33 percent / Li(t-BuO)3AlH / tetrahydrofuran / 0.67 h / -50 °C

3: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

4: 61 mg / TMSOTf / 1,2-dichloro-ethane / 10 h / 90 - 100 °C

With 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jm970275y

upstream raw materials:

(R)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester

Downstream raw materials:

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone

(4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,3-difluoro-dihydro-furan-2-one

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-(methylsulfonyl)-L-erythro-pentofuranose