(4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

Base Information

• Chemical Name: (4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• CAS No.: 38410-80-9
• Molecular Formula: C8H14O4
• Molecular Weight: 174.19
• Hs Code.: 2932999099
• European Community (EC) Number: 625-841-6
• Nikkaji Number: J267.290A
• Mol file: 38410-80-9.mol

Synonyms:38410-80-9;(4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;Methyl (4S)-trans-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;Methyl (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;SCHEMBL1144021;AMY28658;MFCD00077933;AKOS015850897;CS-W021108;DS-16444;O10115;Methyl (4S)-trans-2,2,5-trimethyl-1,3-dioxolane-4carboxylate;(4S)-2,2,5beta-Trimethyl-1,3-dioxolane-4alpha-carboxylic acid methyl ester;1,3-Dioxolane-4-carboxylic acid, 2,2,5-trimethyl-, methyl ester, (4S,5R)-

Chemical Property of (4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

Chemical Property:

• Vapor Pressure: 15.359mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Boiling Point: 243.8 °C at 760 mmHg
• Flash Point: 93.9 °C
• PSA: 44.76000
• Density: 1.044 g/cm³
• LogP: 0.69940
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 188

Purity/Quality:

98% or more ^*data from raw suppliers

Methyl(4S)-trans-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Statements: 10

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(O1)(C)C)C(=O)OC
• Isomeric SMILES: C[C@@H]1[C@H](OC(O1)(C)C)C(=O)OC

Technology Process of (4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

There total 6 articles about (4S,5R)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate 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: 97.0%

(2S,3R)-(-)-methyl 2,3-dihydroxybutanoate (38410-83-2) + 2,2-dimethoxy-propane (77-76-9) → methyl (4S)-trans-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate (38410-80-9)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 2h;

DOI:10.1002/anie.201203176

Reference yield: 72.0%

trans-2,3-Epoxy-buttersaeuremethylester (10133-07-0) + acetone (67-64-1) → cis-2,2,5-Trimethyl-1,3-dioxolan-4-carbonsaeure-methylester (36183-27-4,38410-80-9,38410-81-0,63640-49-3,78086-72-3,81939-14-2,84894-21-3,117181-61-0,151005-02-6)

Guidance literature:

With tin(IV) chloride; In tetrachloromethane; at -35 ℃;

Reference yield: 71.0%

methyl (+/-)-trans-(2,3)-epoxy butanoate (10133-06-9,10133-07-0,10133-45-6,50468-20-7,59123-20-5,83057-88-9,121252-25-3,129311-57-5,136889-92-4,2980-48-5) + acetone (67-64-1) → cis-2,2,5-Trimethyl-1,3-dioxolan-4-carbonsaeure-methylester (36183-27-4,38410-80-9,38410-81-0,63640-49-3,78086-72-3,81939-14-2,84894-21-3,117181-61-0,151005-02-6)

Guidance literature:

With tin(IV) chloride; In tetrachloromethane; 1.) -30 deg C, 30 min, 2.) r.t., 1 h;

upstream raw materials:

(2S,3R)-(-)-methyl 2,3-dihydroxybutanoate

2,2-dimethoxy-propane

(2R,3S)-2,3-Dihydroxy-butyric acid methyl ester

methyl crotonate

Downstream raw materials:

(4S,5R)-2,2,5-Trimethyl-[1,3]dioxolane-4-carboxylic acid

(4S,5R)-2,2,5-trimethyl[1,3]dioxolane-4-carbonyl chloride

(3S,4R)-3,4-(isopropylidenedioxy)-2-propanone

(4R,5S,6S)-2,2,4-Trimethyl-7-methylene-1,3-dioxa-spiro[4.4]nonan-6-ol

Refernces

• 1、 Chen, Junyi,Gill, Adam D.,Hickey, Briana L.,Hooley, Richard J.,Millar, Jocelyn G.,Zhong, Wenwan,Zou, Yunfan. "Enantioselective sensing of insect pheromones in water". supporting information. p. 13341 - 13344. Retrieved 2021/12/17.
• 2、 Bianchi, Paola,Roda, Gabriella,Riva, Sergio,Danieli, Bruno,Zabelinskaja-Mackova, Antonina,Griengl, Herfried. "On the selectivity of oxynitrilases towards α-oxygenated aldehydes". . p. 2213 - 2220. Retrieved 2007/10/03.