METHYL (-)-SHIKIMATE

Base Information

• Chemical Name: METHYL (-)-SHIKIMATE
• CAS No.: 40983-58-2
• Molecular Formula: C8H12O5
• Molecular Weight: 188.18
• Hs Code.: 2918199090
• Mol file: 40983-58-2.mol

Synonyms:methyl (R)-3-hydroxypentanoate;methyl D-(R)-3-hydroxypentanoate;methyl (3R,4S,5R)-3,4,5-trihydroxy-1-cyclohexenecarboxylate;(-)-(3R)-methyl 3-hydroxypentanoate;Methyl (-)-Shikimate;(-)-shikimic acid methyl ester;Pentanoic acid,3-hydroxy-,methyl ester;(S)-Methyl3-Hydroxypentanoate;methyl (3R)-(-)-3-hydroxypentanoate;(R)-(-)-methyl 3-hydroxypentanoate;methyl (3R,4S,5R)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate;(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid methyl ester;D-(-)-methyl-2-hydroxybutanoate;methyl (3R,4S,5R)-shikimate;methyl <7-12C>shikimate;methyl (3R)-hydroxypentanoate;

Chemical Property of METHYL (-)-SHIKIMATE

Chemical Property:

• Vapor Pressure: 3.25E-05mmHg at 25°C
• Melting Point: 114-115°C
• Boiling Point: 317.3°Cat760mmHg
• PKA: 13.48±0.70(Predicted)
• Flash Point: 127.7°C
• PSA: 86.99000
• Density: 1.489g/cm³
• LogP: -1.42780
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Very Slightly, Heated), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

Methyl(-)-Shikimate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: A common biosynthetic precursor

Technology Process of METHYL (-)-SHIKIMATE

There total 166 articles about METHYL (-)-SHIKIMATE 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%

methanol (67-56-1) + shikimic acid (138-59-0) → methyl shikimate (40983-58-2)

Guidance literature:

With Amberlite IR 120; for 16h; Heating;

Reference yield: 100.0%

methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-32-4) → methyl shikimate (40983-58-2)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00431-7

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + shikimic acid (138-59-0) → methyl shikimate (40983-58-2)

Guidance literature:

In methanol; diethyl ether; for 15h; Ambient temperature;

upstream raw materials:

diazomethane

shikimic acid

methanol

(3R,4S,5R)-3,4,5-triacetoxycyclohex-1-ene-1-carboxylic acid

Downstream raw materials:

(2S,3aR,7R,7aS)-7-Hydroxy-2-methyl-2-phenoxycarbonylmethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

(2R,3aR,7R,7aS)-7-Hydroxy-2-methyl-2-phenoxycarbonylmethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

+/-5-epishikimic acid

diethyl hydrazodicarboxylate

Refernces

• 1、 Wang, Dejian,Zhang, Ensheng,Xu, Tianlong,Sheng, Jianfei,Zou, Yong. "Sequential C-C, C-O, and C-N bond-forming reaction of methyl (-)-3-dehydroshikimate, malononitrile, and bromoalkanes: Simple synthesis of 2-(alkylamino)-3-cyanobenzofurans from a biomass-derived substrate". . p. 287 - 293. Retrieved 2016.
• 2、 Oritani, Takayuki,Ueda, Rumi,Kiyota, Hiromasa. "Synthesis of (-)-Methyl Shikimate via Enzymatic Resolution of (1S*, 4R*, 5R*)-4-Hydroxy-6-oxabicyclo[3.2.1]oct-2-en-7-one". . p. 2106 - 2109. Retrieved 2001.
• 3、 Sheng, Jianfei,Liu, Zhihong,Yan, Ming,Zhang, Xuejing,Wang, Dejian,Xu, Jun,Zhang, Ensheng,Zou, Yong. "Biomass-involved synthesis of: N -substituted benzofuro[2,3- d] pyrimidine-4-amines and biological evaluation as novel EGFR tyrosine kinase inhibitors". . p. 4971 - 4977. Retrieved 2017.
• 4、 -. "Novel 4-benzamino-benzofuran[2,3-d]pyridine compound and application thereof". Paragraph 0049-0053. . Retrieved 2019/01/23.