(2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester

Base Information

• Chemical Name: (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester
• CAS No.: 196703-87-4
• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.301
• Mol file: 196703-87-4.mol

Synonyms:(2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester

Chemical Property of (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester

There total 3 articles about (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl 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: 90.0%

(E)-cinnamic acid benzyl ester (103-41-3,8014-16-2) → (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester (196703-87-4)

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 20 ℃; for 24h;

DOI:10.1021/jo010860d

Reference yield:

(E)-cinnamic acid benzyl ester (103-41-3,8014-16-2) → (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester (196703-87-4) + (2S,3R)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester (139165-61-0)

Guidance literature:

With AD-mix-α; methanesulfonamide; water; In tert-butyl alcohol; at 20 ℃; for 24h; Title compound not separated from byproducts.;

DOI:10.1021/jo011172x

Reference yield:

benzy cinnamate (103-41-3,8014-16-2) → (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester (196703-87-4) + (2S,3R)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester (139165-61-0)

Guidance literature:

With potassium osmate; hydroquinine 1,4-phthalazinediyl diether; 4-methylmorpholine N-oxide; In water; tert-butyl alcohol; at 25 ℃; Overall yield = 99 %; Overall yield = 17.9 g;

DOI:10.1021/op030202q

upstream raw materials:

(E)-cinnamic acid benzyl ester

benzy cinnamate

Downstream raw materials:

methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate

(4R,5S)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

benzyl (2S,3R)-3-phenylaziridine-2-carboxylate

L-phenylalanine

Refernces

• 1、 Xiong, Chiyi,Wang, Wei,Cai, Chaozhong,Hruby, Victor J.. "Regioselective and stereoselective nucleophilic ring opening reactions of a phenyl-substituted aziridine: Enantioselective synthesis of β-substituted tryptophan, cysteine, and serine derivatives". . p. 1399 - 1402. Retrieved 2007/10/03.
• 2、 Tagami, Keiko,Takagi, Shuzo,Sano, Shigeki,Shiro, Motoo,Nagao, Yoshimitsu. "Asymmetric dihydroxylation onto the α,β-unsaturated carboxylic ester derivatives of camptothecin". . p. 1663 - 1669. Retrieved 2007/10/03.