(R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

Base Information

• Chemical Name: (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde
• CAS No.: 15186-48-8
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 29329990
• European Community (EC) Number: 676-289-8
• NSC Number: 89869
• Nikkaji Number: J377.033H
• Wikidata: Q76085456
• Mol file: 15186-48-8.mol

Synonyms:1,3-Dioxolane-4-carboxaldehyde,2,2-dimethyl-, (R)-;(4R)-2,2-Dimethyl-1,3-dioxolan-4-carboxaldehyde;(R)-(+)-2,2-Dimethyl-1,3-dioxolan-4-carboxaldehyde;(R)-(+)-Glyceraldehydeacetonide;(R)-2,3-Isopropylidene-D-glyceradehyde;2,3-Di-O-isopropylidene-D-glyceraldehyde;2,3-O-Isopropylidene-(R)-glyceraldehyde;NSC 89869;

Chemical Property of (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

Chemical Property:

• Appearance/Colour: colorless transparent liquid
• Refractive Index: n20/D 1.454(lit.)
• Boiling Point: 166.8 °C at 760 mmHg
• Flash Point: 44.6 °C
• PSA: 35.53000
• Density: 1.123 g/cm³
• LogP: 0.33680
• Storage Temp.: ?20°C
• Solubility.: Difficult to mix.
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 120

Purity/Quality:

98.0%（min） ^*data from raw suppliers

2,3-O-Isopropylidene-D-glyceraldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C=O)C
• Isomeric SMILES: CC1(OC[C@@H](O1)C=O)C
• Uses: (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde is a reactant involved in organic reactions including:? ;Henry condensation reactions1? ;Synthesis of highly functionalized chiral aziridines2? ;Olefination of aldehydes3? ;C-H oxidations4? ;Aldol-type condensations5? ;Synthesis of hydrophilic pyrazine dyes for use as exogenous fluorescent tracer agents6? ;Hosomi-Sakurai reactions7 (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde_x000D__x000D_Discontinued, Unstable (cas# 15186-48-8) is a compound useful in organic synthesis. Reactant involved in organic reactions including:Henry condensation reactionsSynthesis of highly functionalized chiral aziridinesOlefination of aldehydesC-H oxidationsAldol-type condensationsSynthesis of hydrophilic pyrazine dyes for use as exogenous fluorescent tracer agentsHosomi-Sakurai reactions

Technology Process of (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde

There total 47 articles about (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde 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%

[(4R,5R)-5-[(4R,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol (70223-09-5) → 2,3-isopropylidene-glyceraldehyde (15186-48-8)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1016/j.tet.2009.12.024

Reference yield: 96.0%

1,2:5,6-bis-O-(1-methylethylidene)-D-mannitol (102418-34-8) → 2,3-isopropylidene-glyceraldehyde (15186-48-8)

Guidance literature:

With sodium periodate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1039/c5ob01491c

Reference yield: 90.0%

glyceraldehyde (367-47-5,26793-98-6) + 2,2-dimethoxy-propane (77-76-9) → 2,3-isopropylidene-glyceraldehyde (15186-48-8)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 0 - 25 ℃;

upstream raw materials:

1,2:5,6-di-O-isopropylidene-D-mannitol

(2S,3E,5S)-1,2,5,6-tetrahydroxy-1,2:5,6-di-O-isopropylidene-hex-3-ene

5,6-di-O-isopropylidene-D-glucono-1,4-lactone

4,5-isopropylidene-D-arabinose dibenzyl thioacetal

Downstream raw materials:

Phenyl-<(4S)-2,3-di-O-benzyl-4,6-didesoxy-4-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)amino-α-D-galactopyranosyl>-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranosid

N-Phenyl-2,3-O-isopropyliden-D-glyceraldimin

(2R,3R)-3-hydroxy-1,2-O-isopropylidene-3-p-methoxyphenyl-1,2-propanediol

Phenoxy-acetic acid (R)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-3-enyl ester

Refernces

• 1、 Yamaga, Hideomi,Tanino, Keiji. "Synthesis of Substituted Cyclopentenol Derivatives via Intramolecular Addition Reaction of Vinylcopper Species". . p. 230 - 234. Retrieved 2019.
• 2、 Hassan, Najmah P.S.,Naysmith, Briar J.,Sperry, Jonathan,Brimble, Margaret A.. "Formal synthesis of nanaomycin D via a Hauser-Kraus annulation using a chiral enone-lactone". . p. 7137 - 7143. Retrieved 2015.
• 3、 Bilska-Markowska, Monika,Koroniak, Henryk. "Preparation of chiral sugar-derived fluorides using new nucleophilic fluorinating reagents". . p. 185 - 192. Retrieved 2017.
• 4、 Kametani, Tetsuji,Suzuki, Toshio,Sato, Etsuko,Nishimura, Masahiro,Unno, Katsuo. "Synthesis of (3S)-cyclopentanone, Potential Versatile Chiral Synthon for Natural Products from (R)-1,2-Isopropylideneglyceraldehyde". . p. 123 - 124. Retrieved 1982.
• 5、 Hertel,Grossman,Kroin. "Preparation and storage of (R)-2,3-O-isopropylideneglyceraldehyde (D-glyceraldehyde acetonide)". . p. 151 - 154. Retrieved 1991.
• 6、 Hu, Yun-Jin,Huang, Xiao-Dong,Yao, Zhu-Jun,Wu, Yu-Lin. "Formal Synthesis of 3-Deoxy-D-manno-2-Octulosonic Acid (KDO) via a Highly Double-Stereoselective Hetero Diels-Alder Reaction Directed by a (Salen)CoII Catalyst and Chiral Diene". . p. 2456 - 2461. Retrieved 1998.
• 7、 Chandler,Howarth,Crout. "Measuring stereoselectivity in lipase-catalyzed acidolysis reactions by ultra-high resolution 13C nuclear magnetic resonance". . p. 953 - 958. Retrieved 2001.
• 8、 Wu, Shaoping,Zhang, Yongmin,Agarwal, Jyoti,Mathieu, Emilie,Thorimbert, Serge,Dechoux, Luc. "Studies towards the synthesis of secoiridoids". . p. 7663 - 7669. Retrieved 2015.
• 9、 Koenig, Stefan G.,Loewe, Ralf S.,Austin, David J.. "An improved synthesis of (4S)-4,5-O-isopropylidenepent- (2Z)-enoate". . p. 1379 - 1383. Retrieved 2002.
• 10、 Kamimura, Akio,Shiramatsu, Yuto,Murata, Kengo,Kawamoto, Takuji. "Solubility-switchable ionic liquids: A control of hydrophilicity and hydrophobicity using a protective group". . p. 1079 - 1081. Retrieved 2018.