Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate

Base Information

• Chemical Name: Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate
• CAS No.: 114420-06-3
• Molecular Formula: C10H16 F2 O5
• Molecular Weight: 254.231
• Hs Code.: 2932999099
• European Community (EC) Number: 821-786-9
• Mol file: 114420-06-3.mol

Synonyms:114420-06-3;Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate;ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate;95058-92-7;PENTONIC ACID, 2-DEOXY-2,2-DIFLUORO-4,5-O-(1-METHYLETHYLIDENE)-, ETHYL ESTER;Ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropionate;2-Deoxy-2,2-difluoro-4,5-O-isopropylidene-D-erythro-pentonic Acid Ethyl Ester;SCHEMBL2251318;(R)-Ethyl 3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate;ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxy-propanoate;AKOS015912182;DS-0785;EN300-1703549;A845158;ethyl 2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)-propionate;3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoic acid ethyl ester;ethyl 3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-bis(fluoranyl)-3-oxidanyl-propanoate;Pentonic acid,2-deoxy-2,2-difluoro-4,5-O-(1-methylethylidene)-,ethyl ester

Chemical Property of Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate

Chemical Property:

• Vapor Pressure: 6.67E-06mmHg at 25°C
• Boiling Point: 338.4°C at 760 mmHg
• PKA: 11.95±0.20(Predicted)
• Flash Point: 158.5°C
• PSA: 64.99000
• Density: 1.232g/cm³
• LogP: 0.69720
• Storage Temp.: 2-8°C
• 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

Ethyl3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-difluoro-3-hydroxypropanoate 95+% ^*data from reagent 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

Technology Process of Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate

There total 4 articles about Ethyl (3R,S)-2,2-difluoro-3-hydroxy-3-(2,2-dimethyldioxolan-4-yl)propionate 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:

Ethyl bromodifluoroacetate (667-27-6) + (d,l) isopropylidene glyceraldehyde (5736-03-8) → ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate (114420-06-3,166376-97-2)

Guidance literature:

With chloro-trimethyl-silane; zinc; In tetrahydrofuran; at 60 - 70 ℃; for 2.16667h; Inert atmosphere; Industrial scale;

Reference yield:

5,6-0-isopropylidene ascorbic acid (860649-42-9) → ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate (114420-06-3,166376-97-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate; dihydrogen peroxide / water / 5 h / 20 - 40 °C / Industrial scale

2: sodium acetate trihydrate; acetic acid; sodium hypochlorite / water / 1 h / 25 - 45 °C / Industrial scale

3: zinc; chloro-trimethyl-silane / tetrahydrofuran / 2.17 h / 60 - 70 °C / Inert atmosphere; Industrial scale

With sodium hypochlorite; chloro-trimethyl-silane; dihydrogen peroxide; sodium acetate trihydrate; sodium carbonate; acetic acid; zinc; In tetrahydrofuran; water;

Reference yield:

C7H12O5 → ethyl 2-deoxy-2,2-difluoro-D-erythro,D-threo-pentonate (114420-06-3,166376-97-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate trihydrate; acetic acid; sodium hypochlorite / water / 1 h / 25 - 45 °C / Industrial scale

2: zinc; chloro-trimethyl-silane / tetrahydrofuran / 2.17 h / 60 - 70 °C / Inert atmosphere; Industrial scale

With sodium hypochlorite; chloro-trimethyl-silane; sodium acetate trihydrate; acetic acid; zinc; In tetrahydrofuran; water;

upstream raw materials:

Ethyl bromodifluoroacetate

(d,l) isopropylidene glyceraldehyde

5,6-0-isopropylidene ascorbic acid

Downstream raw materials:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

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

Refernces

• 1、 -. "Difluoro antivirals and intermediate therefor". . . Retrieved 2008/06/13.