Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate

Base Information

• Chemical Name: Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate
• CAS No.: 95422-24-5
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• Hs Code.: 2932999099
• European Community (EC) Number: 804-315-1
• Nikkaji Number: J507.460F
• Mol file: 95422-24-5.mol

Synonyms:95422-24-5;Methyl (S)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetate;Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate;(S)-methyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate;MFCD00274220;SCHEMBL4528384;methyl 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetate;AEMMCWMMNLSHFT-LURJTMIESA-N;VDA42224;1,3-Dioxolane-4-acetic acid, 2,2-dimethyl-, methyl ester, (4S)-;AC2354;CS-12355;CS-0318973;A23110;methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-acetate;Methyl(S)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetate;(S)-2,2-Dimethyl-1,3-dioxolane-4-acetic acid methyl ester;1,3-Dioxolane-4-aceticacid,2,2-dimethyl-,methyl ester,(4S)-;Methyl (S)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetate ee;Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate, 97%

Chemical Property of Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate

Chemical Property:

• Vapor Pressure: 0.331mmHg at 25°C
• Refractive Index: n20/D 1.615(lit.)
• Boiling Point: 200 °C at 760 mmHg
• Flash Point: 76.1 °C
• PSA: 44.76000
• Density: 1.044 g/cm³
• LogP: 0.70100
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-Methyl 2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OCC(O1)CC(=O)OC)C
• Isomeric SMILES: CC1(OC[C@@H](O1)CC(=O)OC)C

Technology Process of Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate

There total 15 articles about Methyl (4S)-(+)-2,2-dimethyl-1,3-dioxolane-4-acetate 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: 95.0%

methyl (3S)-3,4-dihydroxybutyrate (90414-36-1) + 2,2-dimethoxy-propane (77-76-9) → methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5)

Guidance literature:

With toluene-4-sulfonic acid; for 1h; Ambient temperature;

DOI:10.1080/00397919208021080

Reference yield: 83.0%

(3S)-hydroxy-γ-butyrolactone (5469-16-9,58081-05-3,131432-37-6,7331-52-4) + 2,2-dimethoxy-propane (77-76-9) → methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 14h;

DOI:10.1016/j.tet.2010.01.043

Reference yield: 82.0%

(R)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-methanesulfonyloxy-acetic acid methyl ester → methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5)

Guidance literature:

With diphenyl diselenide; sodium perchlorate; diethyl malonate; In N,N-dimethyl-formamide; at 50 ℃; for 7.3h; electroreduction, 5.0 F mol^-1;

DOI:10.1246/bcsj.65.3200

upstream raw materials:

methanol

2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

2-Methoxypropene

methyl (3S)-3,4-dihydroxybutyrate

Downstream raw materials:

(S)-3,4-O-isopropylidene-3,4-dihydroxybutyltriphenylphosphonium iodide

(6Z,9S)-6-ethylidene-9-p-toluenesulfonyloxymethyl-9-nonanolide

1-[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-2-oxo-cyclohexanecarboxylic acid ethyl ester

(R)-(-)-phoracantholide I

Refernces

• 1、 Bauder, Claude. "Toward an Asymmetric Synthesis of Bistramide K". . p. 4874 - 4899. Retrieved 2018/09/10.
• 2、 Venkanna, Arramshetti,Sreedhar, Eppakayala,Siva, Bandi,Babu, Katragadda Suresh,Prasad, Kothakonda Rajendra,Rao, Janaswamy Madhusudana. "Studies directed towards the total synthesis of koshikalide: Stereoselective synthesis of the macrocyclic core". . p. 1010 - 1022. Retrieved 2013/09/23.