Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate

Base Information

• Chemical Name: Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate
• CAS No.: 928797-50-6
• Molecular Formula: C10H16F2O5
• Molecular Weight: 254.231
• DSSTox Substance ID: DTXSID00541766
• Mol file: 928797-50-6.mol

Synonyms:928797-50-6;Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate;Ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-difluoro-3-hydroxypropanoate;SCHEMBL10048611;DTXSID00541766;OUFRYOWGFSOSEY-ULUSZKPHSA-N;Ethyl3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate

Chemical Property of Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 338.388°C at 760 mmHg
• PKA: 11.95±0.20(Predicted)
• Flash Point: 158.451°C
• PSA: 64.99000
• Density: 1.232g/cm³
• LogP: 0.69720
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 254.09657993
• Heavy Atom Count: 17
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(C1COC(O1)(C)C)O)(F)F
• Isomeric SMILES: CCOC(=O)C(C([C@H]1COC(O1)(C)C)O)(F)F

Technology Process of Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate

There total 4 articles about Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate 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: 74.1%

Ethyl bromodifluoroacetate (667-27-6) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate (928797-50-6,166376-97-2)

Guidance literature:

With chloro-trimethyl-silane; zinc; In tetrahydrofuran; diethyl ether; ethylene dibromide; at 48 - 50 ℃; for 5h;

Reference yield:

1,2:5,6-di-O-isopropylidene-D-mannitol (1707-77-3) → ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate (928797-50-6,166376-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydrogencarbonate; sodium periodate / water; tetrahydrofuran / 2.5 h / 18 °C / Cooling with ice

2: zinc; chloro-trimethyl-silane / tetrahydrofuran; diethyl ether; ethylene dibromide / 5 h / 48 - 50 °C

With sodium periodate; chloro-trimethyl-silane; potassium hydrogencarbonate; zinc; In tetrahydrofuran; diethyl ether; water; ethylene dibromide;

Reference yield:

5,6-O-isopropylidene-D-isoascorbic acid (50271-42-6) → ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate (928797-50-6,166376-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: dihydrogen peroxide / Large scale

2: acetic acid; sodium hypochlorite / water / Large scale

3: zinc / tetrahydrofuran / 2 h / 60 - 70 °C / Large scale

With sodium hypochlorite; dihydrogen peroxide; acetic acid; zinc; In tetrahydrofuran; water;

upstream raw materials:

Ethyl bromodifluoroacetate

2,3-isopropylidene-glyceraldehyde

1,2:5,6-di-O-isopropylidene-D-mannitol

5,6-O-isopropylidene-D-isoascorbic acid

Downstream raw materials:

ethyl (3RS)-3-(benzoyloxy)-2,2-difluoro-3-(2,2-dimethyldioxolan-4-yl)propionate

2,6-lutidine hydrochloride

2-deoxy-2,2-difluoro-1-carbonylribose

ethyl 2,2-difluoro-3-(4-methoxyphenylcarbamoyl)-3-(2,2-dimethyldioxolan-4-yl)propionate