(4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde

Base Information

• Chemical Name: (4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde
• CAS No.: 32233-44-6
• Molecular Formula: C7H12 O3
• Molecular Weight: 144.17
• European Community (EC) Number: 845-243-0
• DSSTox Substance ID: DTXSID20454541
• Nikkaji Number: J826.512G
• Wikidata: Q72469845
• Mol file: 32233-44-6.mol

Synonyms:32233-44-6;(4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde;2-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]acetaldehyde;(S)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde;SCHEMBL3054401;1,3-Dioxolane-4-acetaldehyde, 2,2-dimethyl-, (4S)-;DTXSID20454541;MFCD09751032;AKOS006239987;CS-0356408;2,2-Dimethyl-1,3-dioxolane-4beta-acetaldehyde;EN300-7278221;[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]acetaldehyde;Z1198222787

Chemical Property of (4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde

Chemical Property:

• Boiling Point: 73-74 °C(Press: 11 Torr)
• PSA: 35.53000
• Density: 1.000±0.06 g/cm3(Predicted)
• LogP: 0.72690
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 144.078644241
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

98%Min ^*data from raw suppliers

(4S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETALDEHYDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde

There total 19 articles about (4S)-2,2-dimethyl-1,3-dioxolane-4-acetaldehyde 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%

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5) → 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6)

Guidance literature:

With diisobutylaluminium hydride; at -78 ℃; Inert atmosphere;

DOI:10.1021/jo100094d

Reference yield: 90.0%

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) → 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6)

Guidance literature:

With dipyridine chromium trioxide;

DOI:10.1016/S0040-4039(98)00686-8

Reference yield: 90.0%

2-deoxy-3,4-O-isopropylidene-D-glycero-tetrose diethyldithioacetal (111205-95-9) → 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde (32233-44-6)

Guidance literature:

With water; mercury dichloride; mercury(II) oxide; In acetone; Ambient temperature;

DOI:10.1016/S0957-4166(99)00072-5

upstream raw materials:

4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

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

(S)-Malic acid

dimethyl (S)-malate

Downstream raw materials:

(1'S,3R,5S)-3,5,6-trihydroxy-5,6-O-isopropylidenehexanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester

(1'S,3S,5S)-3,5,6-trihydroxy-5,6-O-isopropylidenehexanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester

2-[3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-propyl]-oxazole-4-carboxylic acid methyl ester

2-methyl-oxazole-4-carboxylic acid methyl ester

Refernces

• 1、 Hermitage, Stephen A.,Roberts, Stanley M.,Watson, Daniel J.. "Approaches to the C-24 to C-37 perimeter of Altohyrtin A". . p. 3567 - 3570. Retrieved 1998.
• 2、 Veerasamy, Nagarathanam,Ghosh, Ankan,Li, Jinming,Watanabe, Kazuhiro,Serrill, Jeffrey D.,Ishmael, Jane E.,McPhail, Kerry L.,Carter, Rich G.. "Enantioselective Total Synthesis of Mandelalide A and Isomandelalide A: Discovery of a Cytotoxic Ring-Expanded Isomer". supporting information. p. 770 - 773. Retrieved 2016/02/05.
• 3、 Gamedze, Makhosazana P.,Nkambule, Comfort M.. "Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols". supporting information. p. 1825 - 1829. Retrieved 2015/03/30.