Dodecyl alpha-D-glucopyranoside

Base Information

• Chemical Name: Dodecyl alpha-D-glucopyranoside
• CAS No.: 29980-16-3
• Molecular Formula: C18H36O6
• Molecular Weight: 348.48
• European Community (EC) Number: 249-988-7
• DSSTox Substance ID: DTXSID301310835
• Nikkaji Number: J249.899E
• Mol file: 29980-16-3.mol

Synonyms:Dodecyl alpha-D-glucopyranoside;29980-16-3;Dodecyl a-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-dodecoxy-6-(hydroxymethyl)oxane-3,4,5-triol;EINECS 249-988-7;C18-H36-O6;a-D-Glucopyranoside,dodecyl;SCHEMBL60523;dodecyl-alpha-d-glucopyranoside;Dodecyl-I+/--D-glucopyranoside;DTXSID301310835;.alpha.-D-Glucopyranoside, dodecyl;J-017719;(2S,3R,4S,5S,6R)-2-(DODECYLOXY)-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL;(2S,3R,4S,5S,6R)-2-(Dodecyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property of Dodecyl alpha-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 4.72E-12mmHg at 25°C
• Refractive Index: 1.508
• Boiling Point: 499.1 °C at 760 mmHg
• Flash Point: 255.6 °C
• PSA: 99.38000
• Density: 1.12 g/cm³
• LogP: 1.72380
• Storage Temp.: −20°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 348.25118886
• Heavy Atom Count: 24
• Complexity: 301

Purity/Quality:

98% ^*data from raw suppliers

Dodecyl a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CCCCCCCCCCCCO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

Technology Process of Dodecyl alpha-D-glucopyranoside

There total 29 articles about Dodecyl alpha-D-glucopyranoside 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%

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside (66854-07-7,103129-55-1,117076-31-0) → n-dodecanyl β-D-galactopyranoside (6801-92-9,29781-83-7,29980-16-3,59122-55-3,102043-71-0)

Guidance literature:

With ammonium hydroxide; In methanol; for 3h; Reflux;

DOI:10.1016/j.bmcl.2012.01.069

Reference yield: 94.0%

dodecyl 4,6-O-benzylidene-β-D-galactopyrnoside (1427214-08-1) → n-dodecanyl β-D-galactopyranoside (6801-92-9,29781-83-7,29980-16-3,59122-55-3,102043-71-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; chloroform;

DOI:10.1016/j.tetlet.2013.01.025

Reference yield: 70.0%

dodecyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside → n-dodecanyl β-D-galactopyranoside (6801-92-9,29781-83-7,29980-16-3,59122-55-3,102043-71-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 72h;

DOI:10.1080/07328300500208107

upstream raw materials:

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

1-dodecyl alcohol

4-nitrophenyl-β-D-galactopyranoside

β-D-galactose peracetate

Downstream raw materials:

dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-β-D-galactopyranoside

dodecyl 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl-(1->2)-3,4-O-isopropylidene-β-D-galactopyranoside

dodecyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-β-D-galactopyranoside

dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Refernces

• 1、 Bogdanová, Kate?ina,Combet, Sophie,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marian,Kanjaková, Nina,Klunda, Tomá?,Kolá?, Milan,Poláková, Monika,Uhríková, Daniela. "Antimicrobial and cytotoxic activity of (thio)alkyl hexopyranosides, nonionic glycolipid mimetics". . . Retrieved 2020/01/30.
• 2、 Voggel, Michael,Meinusch, Rebecca M.,Siewert, Vanessa,Kunkel, Marius,Wittmann, Valentin,Polarz, Sebastian. "Sweet surfactants: Packing parameter-invariant amphiphiles as emulsifiers and capping agents for morphology control of inorganic particles". . p. 7214 - 7227. Retrieved 2018/09/26.