(-)-4-epi-Shikimic acid

Base Information

• Chemical Name: (-)-4-epi-Shikimic acid
• CAS No.: 21967-35-1
• Molecular Formula: C7H10O5
• Molecular Weight: 174.15
• Mol file: 21967-35-1.mol

Synonyms:(3R,4R,5R)-3,4,5-Trihydroxy-cyclohex-1-enecarboxylic acid;4-epi-Shikimisaeure;shikimic acid;(-)-4-epi-shikimic acid;Shikimisaeure;

Chemical Property of (-)-4-epi-Shikimic acid

Chemical Property:

• PSA: 97.99000
• LogP: -1.51620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-4-epi-Shikimic acid

There total 49 articles about (-)-4-epi-Shikimic acid 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: 99.0%

(-)-methyl 4-epi-shikimate (897014-96-9) → (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid (21967-35-1)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; for 2h; Inert atmosphere;

DOI:10.1021/ol201252x

Reference yield: 96.0%

(-)-methyl 4,5-O-benzylidene-4-epi-shikimate (94903-41-0) → (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid (21967-35-1)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/jo00206a035

Reference yield: 90.0%

(3aR,7R,7aS)-methyl 7-hydroxy-2,2-dimethyl-3a,4,7,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate (104464-18-8) → (3R,4R,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid (21967-35-1)

Guidance literature:

With trifluoroacetic acid; In water; for 12h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo402764v

upstream raw materials:

(-)-methyl 4,5-O-benzylidene-4-epi-shikimate

(3R,4R,5R)-4,5-Diacetoxy-3-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohex-1-enecarboxylic acid methyl ester

methyl (3R,4R,5R)-3-O-benzoyl-3,4,5-trihydroxycyclohex-1-ene-1-carboxylate

methyl (3S,4R,5R)-3-O-benzoyl-4,5-O-cyclohexylidene-3,4,5-trihydroxycyclohec-1-ene-1-carboxylate

Downstream raw materials:

(-)-methyl 4-epi-shikimate

methyl 3,4,5-tri-O-acetyl-4-epi-shikimate

Refernces

• 1、 Ananthan, Bakthavachalam,Chang, Wan-Chun,Lin, Jhe-Sain,Li, Pin-Hui,Yan, Tu-Hsin. "A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol". . p. 2898 - 2905. Retrieved 2014/05/06.
• 2、 Schaub, Christoph,Mueller, Bernd,Schmidt, Richard R.. "Sialyltransferase inhibitors based on CMP-quinic acid". . p. 1745 - 1758. Retrieved 2007/10/03.