2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER

Base Information

• Chemical Name: 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER
• CAS No.: 166376-98-3
• Molecular Formula: C₁₀H₁₆F₂O₅
• Molecular Weight: 254.231
• Mol file: 166376-98-3.mol

Synonyms:2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER

Chemical Property of 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.428
• Boiling Point: 338.388°C at 760 mmHg
• Flash Point: 158.451°C
• PSA: 64.99000
• Density: 1.232g/cm³
• LogP: 0.69720

Purity/Quality:

98.5% ^*data from raw suppliers

2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER

There total 2 articles about 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-L-THREO-PENTONIC ACID, ETHYL ESTER 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: 8.0%

Ethyl bromodifluoroacetate (667-27-6) + (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde (22323-80-4) → (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) + (S)-3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propionic acid ethyl ester

Guidance literature:

With zinc; In tetrahydrofuran; diethyl ether; at 50 ℃; for 0.5h;

DOI:10.1021/jm970275y

Reference yield:

5,6-O-isopropylidene-L-gluono-1,4-lactone → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / NaIO₄, 2N aq. NaOH / 2 h / Ambient temperature

2: 35 percent / Zn / diethyl ether; tetrahydrofuran / 0.5 h / 50 °C

With sodium hydroxide; sodium periodate; zinc; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm970275y

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) → 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-fluorocytosine (197452-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: Dowex-50 (H⁺) resin, H₂O / methanol / 120 h

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

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

4: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) HMDS, (NH₄)2SO₄, 2.) TMSOTf / 1.) 125 deg C, 4 h, 2.) dichloroethane, from 90 to 100 deg C, 10 h

With 2,6-dimethylpyridine; ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; Dowex-50 (H⁺) resin; water; lithium tri-t-butoxyaluminum hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm970275y

upstream raw materials:

Ethyl bromodifluoroacetate

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Downstream raw materials:

(4S,5S)-3,3-Difluoro-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one

(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-L-erythro-pentono-γ-lactone

Refernces