(1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester

Base Information

• Chemical Name: (1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester
• CAS No.: 227783-08-6
• Molecular Formula: C10H16O4
• Molecular Weight: 200.235
• DSSTox Substance ID: DTXSID101256051
• Nikkaji Number: J1.097.967F
• Mol file: 227783-08-6.mol

Synonyms:D-camphoric acid;L-camphoric acid;

Chemical Property of (1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester

Chemical Property:

• Boiling Point: 317.4±35.0 °C(Predicted)
• PKA: 4.41±0.10(Predicted)
• PSA: 63.60000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 1.44050
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

(1R,3S)-1,3-CyclohexanedicarboxylicAcid1-Ethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1CCCC(C1)C(=O)O
• Isomeric SMILES: CCOC(=O)[C@@H]1CCC[C@@H](C1)C(=O)O
• Uses: (1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester is used in the synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase.

Technology Process of (1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester

There total 3 articles about (1R,3S)-1,3-Cyclohexanedicarboxylic Acid 1-Ethylester 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%

cis-1,3-Cyclohexanedicarboxylic acid diethyl ester (62059-56-7) → (1S,3R)-3-ethoxycarbonylcyclohexane-1-carboxylic acid (227783-08-6)

Guidance literature:

With phosphate buffer; lipase AYS Amano; at 20 ℃; for 24h; pH=7.2;

DOI:10.1016/j.bmc.2005.01.033

Reference yield:

(1R)-cyclohexane-1,3-dicarboxylic acid (2305-30-8,2305-31-9,3971-31-1,21917-23-7,116724-13-1,116724-14-2) → (1S,3R)-3-ethoxycarbonylcyclohexane-1-carboxylic acid (227783-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetyl chloride / Reflux

1.2: Reflux

2.1: Amano Lipase AYS / aq. phosphate buffer / 20 °C / pH 7.2

With acetyl chloride; In aq. phosphate buffer;

DOI:10.1021/acs.oprd.6b00063

Reference yield:

3-oxabicyclo<3.3.1>nonane-2,4-dione (4355-31-1) → (1S,3R)-3-ethoxycarbonylcyclohexane-1-carboxylic acid (227783-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / ethanol

2: Amano Lipase AYS / aq. phosphate buffer / 20 °C / pH 7.2

With toluene-4-sulfonic acid; In aq. phosphate buffer; ethanol;

DOI:10.1021/acs.oprd.6b00063

upstream raw materials:

cis-1,3-Cyclohexanedicarboxylic acid diethyl ester

(1R)-cyclohexane-1,3-dicarboxylic acid

3-oxabicyclo<3.3.1>nonane-2,4-dione

Downstream raw materials:

N-[(1R,3S)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]-pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]morpholine-4-carboxamide

tert-butyl N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]carbamate

N-[(1R,3S)-3-[[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]amino]cyclohexyl]morpholine-4-carboxamide

(1S,3R)-N₁-[5-fluoro-2-[5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-4-yl]cyclohexane-1,3-diamine

Refernces

• 1、 Yamazaki, Kazuo,Kaneko, Yasushi,Suwa, Kie,Ebara, Shinji,Nakazawa, Kyoko,Yasuno, Kazuhiro. "Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure". . p. 2509 - 2522. Retrieved 2007/10/03.
• 2、 -. "STEREOSELECTIVE PROCESS FOR PREPARING CYCLOHEXYL AMINE DERIVATIVES". Page 46. . Retrieved 2010/02/14.