5-Ethenyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

• Chemical Name: 5-Ethenyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS No.: 4105-60-6
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.181
• DSSTox Substance ID: DTXSID90557154
• Mol file: 4105-60-6.mol

Synonyms:4105-60-6;SCHEMBL12940551;DTXSID90557154;AKOS006330778;4,5-Dideoxy-2,3-O-(1-methylethylidene)pent-4-enose

Chemical Property of 5-Ethenyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Chemical Property:

• Vapor Pressure: 0.17mmHg at 25°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.078644241
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

99% ^*data from raw suppliers

2,2-DIMETHYL-5-VINYL-(1,3)DIOXOLANE-4-CARBALDEHYDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC(C(O1)C=O)C=C)C

Technology Process of 5-Ethenyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 8 articles about 5-Ethenyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde 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: 92.0%

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol (114817-96-8) → 2,3-O-isopropylidene-D-threo-4-pentenose (4105-60-6)

Guidance literature:

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol; With sulfur trioxide pyridine complex; triethylamine; In dichloromethane; at -10 ℃; for 0.0833333h; Inert atmosphere;

With dimethylsulfone; In dichloromethane; for 0.25h; Inert atmosphere;

DOI:10.1002/ejoc.201300434

Reference yield: 90.0%

(1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol (168109-89-5) → 2,3-O-isopropylidene-D-threo-4-pentenose (4105-60-6)

Guidance literature:

With sodium periodate; In water; at 0 ℃; for 1.5h;

DOI:10.1016/j.tet.2005.01.004

Reference yield:

(4S,4'R,5R)-2,2,2',2'-tetramethyl-5-vinyl-4,4'-bi(1,3-dioxolane) (4239-90-1,22893-94-3) → 2,3-O-isopropylidene-D-threo-4-pentenose (4105-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / Zn(NO₃)2*6H₂O / acetonitrile / 24 h / 20 °C

2: 90 percent / NaIO₄ / H₂O / 1.5 h / 0 °C

With zinc(II) nitrate; sodium periodate; In water; acetonitrile;

DOI:10.1016/j.tet.2005.01.004

upstream raw materials:

[(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol

(1R)-1-((4R,5R)-2,2-dimethyl-5-vinyl[1,3]dioxolan-4-yl)ethane-1,2-diol

(4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

(3R,4R)-5-(tert-butyldimethylsiloxy)-3,4-(isopropylidenedioxy)pent-1-ene

Downstream raw materials:

(R)-2-[((4R,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-5-isopropenyl-cyclohexanone

(R)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol

(S)-((4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)(phenyl)methanol

(1R,2R,3S)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)but-3-enyl]tetrahydrofuran-2-yl}-2-(4-methoxybenzyloxy)-3-methylhex-5-yn-1-ol

Refernces

• 1、 Liu, Jun,Gao, Yangguang,Wang, Linlin,Du, Yuguo. "Chiron approach for the total synthesis of (+)-synargentolide B". . p. 6443 - 6447. Retrieved 2017/10/09.
• 2、 Sarabia, Francisco,Martín-Gálvez, Francisca,García-Ruiz, Cristina,Sánchez-Ruiz, Antonio,Vivar-García, Carlos. "Epi -, Epoxy-, and C2-modified bengamides: Synthesis and biological evaluation". . p. 5239 - 5253. Retrieved 2013/07/26.