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

Base Information

• Chemical Name: Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate
• CAS No.: 78086-72-3
• Molecular Formula: C8H14 O4
• Molecular Weight: 174.19
• Hs Code.: 2932999099
• European Community (EC) Number: 628-440-4
• DSSTox Substance ID: DTXSID60357426
• Nikkaji Number: J2.027.935D
• Wikidata: Q72492193
• Mol file: 78086-72-3.mol

Synonyms:78086-72-3;Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;(4R,5S)-Methyl 2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;Methyl (2R,3S)-2,3-O-isopropylidene-2,3-dihydroxybutyrate;MFCD00077802;SCHEMBL7204854;DTXSID60357426;AKOS015850838;AKOS015915846;CS-W000681;DS-16457;F51894;A839332;(4R,5S)-Methyl2,2,5-trimethyl-1,3-dioxolane-4-carboxylate;Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate, technical, >=90% (sum of enantiomers, GC)

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

Chemical Property:

• Vapor Pressure: 0.0314mmHg at 25°C
• Refractive Index: n20/D 1.422
• Boiling Point: 243.8°C at 760 mmHg
• Flash Point: 50 ºC
• PSA: 44.76000
• Density: 1.06
• 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:

97% ^*data from raw suppliers

Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate technical, ≥90% (sum of enantiomers, GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:
• Hazard Codes: R10:
• 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 Methyl (4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylate

There total 2 articles about Methyl (4R,5S)-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: 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;

Reference yield: 57.0%

benzyloxyacetoaldehyde (60656-87-3) + (2R,3S)-4-desoxy-2,3-O-isopropylidene-L-threonate de methyle (78086-72-3) → (4R,5S)-2-Benzyloxymethyl-5-methyl-[1,3]dioxolane-4-carboxylic acid methyl ester (809277-06-3)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; at 80 ℃; for 1h;

DOI:10.1016/j.bmc.2004.08.054

upstream raw materials:

methyl (+/-)-trans-(2,3)-epoxy butanoate

acetone

trans-2,3-Epoxy-buttersaeuremethylester

Downstream raw materials:

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

(4R,5S)-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid

(-)-1-O-p-toluenesulfonyl-4-deoxy-L-threytol

(4S,5S)-4-hydroxymethyl-2,2,5-trimethyl-[1,3]-dioxolane