diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate

Base Information

• Chemical Name: diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate
• CAS No.: 173657-53-9
• Molecular Formula: C₁₂H₁₉O₅P
• Molecular Weight: 274.254
• Mol file: 173657-53-9.mol

Synonyms:diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate

Chemical Property of diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate

There total 2 articles about diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate 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%

diethyl (E)-(2-phenylethenyl)phosphonate (20408-33-7) → diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate (173657-53-9)

Guidance literature:

With methanesulfonamide; AD-mix-β; In water; tert-butyl alcohol; at 0 - 20 ℃; for 96h;

DOI:10.1016/S0957-4166(03)00177-0

Reference yield:

diethyl (E)-(2-phenylethenyl)phosphonate (20408-33-7) → diethyl (1S,2S)-1,2-dihydroxy-2-phenylethylphosphonate (164358-33-2) + diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate (173657-53-9)

Guidance literature:

With AD-mix-α; methanesulfonamide; water; tert-butyl alcohol; at 25 ℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/0957-4166(95)00014-G

Reference yield: 90.0%

diethyl (1R,2R)-1,2-dihydroxy-2-phenylethylphosphonate (173657-53-9) → 4-phenyl-5-diethylphosphonyl-1,2,3-dioxathiolane-2-oxide

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃;

upstream raw materials:

diethyl (E)-(2-phenylethenyl)phosphonate

Refernces

• 1、 Yokomatsu, Tsutomu,Yamagishi, Takehiro,Suemune, Kenji,Yoshida, Yoshinori,Shibuya, Shiroshi. "Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents". . p. 767 - 780. Retrieved 2007/10/03.
• 2、 Lohray, B. B.,Maji, D. K.,Nandanan, E.. "Stereoselective synthesis of dihydroxyphosphonates via asymmetric dihydroxylation of unsaturated phosphonate esters: Synthesis of hydroxyaminophosphonates via cyclic sulfites". . p. 1023 - 1025. Retrieved 2007/10/03.