Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-D-Glucopyranoside

Base Information

• Chemical Name: Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-D-Glucopyranoside
• CAS No.: 18449-82-6
• Molecular Formula: C₂₆H₅₀O₁₁
• Molecular Weight: 538.676
• European Community (EC) Number: 606-032-7
• DSSTox Substance ID: DTXSID80433039
• Nikkaji Number: J747.841K
• Mol file: 18449-82-6.mol

Synonyms:18449-82-6;N-TETRADECYL-BETA-D-MALTOSIDE;Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-D-Glucopyranoside;Tetradecyl-|A-D-maltoside;Tetradecyl b-D-maltopyranoside;Tetradecyl 4-O-a-D-glucopyranosyl-b-D-glucopyranoside;(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-tetradecoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;(2R,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(tetradecyloxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;Tetradecyl beta-maltoside;n-Tetradecyl-b-D-maltoside;SCHEMBL411273;n-Tetradecyl-b-D-maltopyranosid;DTXSID80433039;UKPROSIGWJBJGA-IWODYCRQSA-N;HY-W337897;AS-77854;CS-0449226;Tetradecyl-beta-D-maltoside, >=99.0% (TLC);W-201657;Q27462602;(2R,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(tetradecyloxy)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-DIHYDROXY-2-(HYDROXYMETHYL)-6-(TETRADECYLOXY)OXAN-3-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL

Chemical Property of Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-D-Glucopyranoside

Chemical Property:

• PSA: 178.53000
• LogP: 0.32820
• Storage Temp.: −20°C
• Solubility.: H2O: soluble10mg/mL, clear, colorless
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 18
• Exact Mass: 538.33531241
• Heavy Atom Count: 37
• Complexity: 583

Purity/Quality:

98%,99%, ^*data from raw suppliers

Tetradecyl b-D-maltopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCOC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
• Isomeric SMILES: CCCCCCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
• Uses: Tetradecyl-β-D-maltoside (CAS# 18449-82-6) is an alkylglycoside surfactant proposed as a drug delivery excipient with the potential to enhance mucosal drug absorption of therapeutic macromolecules.

Technology Process of Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-D-Glucopyranoside

There total 4 articles about Tetradecyl 4-O-Alpha-D-Glucopyranosyl-Beta-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: 86.9%

1-tetradecyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (18449-81-5) → tetradecyl-β-D-maltoside (7084-67-5,122119-57-7,124616-48-4,124616-49-5,124616-50-8,18449-82-6)

Guidance literature:

With methanol; sodium methylate; for 4h; pH=Ca. 10;

Reference yield: 80.0%

tetradecyl hepta-O-acetyl-β-maltoside → tetradecyl-β-D-maltoside (7084-67-5,122119-57-7,124616-48-4,124616-49-5,124616-50-8,18449-82-6)

Guidance literature:

With water; triethylamine; In methanol; at 20 - 50 ℃; for 18h; Inert atmosphere;

DOI:10.1134/S1070428020100231

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8) → tetradecyl-β-D-maltoside (7084-67-5,122119-57-7,124616-48-4,124616-49-5,124616-50-8,18449-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 6.5 h / 20 °C / Molecular sieve; Cooling with ice

2: sodium methylate; methanol / 4 h / pH Ca_. 10

With methanol; boron trifluoride diethyl etherate; sodium methylate; In dichloromethane;

upstream raw materials:

1-tetradecyl-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate

1-Tetradecanol

Refernces

• 1、 Elias, M.,Hossain, M. A.,Jamil, M. A. R.,Rahman, M. M.,Siddiki, S. M. A. Hakim. "Highly β-Selective Glycosylation Reactions for the Synthesis of ω-Functionalized Alkyl β-Maltoside as a Co-crystallizing Detergent". . p. 1806 - 1814. Retrieved 2020/12/01.
• 2、 Markovic, Zoran,Predojevic, Jasmina,Manojlovic, Nedeljko T.. "Synthesis of C7-C16-Alkyl maltosides in the presence of tin(IV) chloride as a lewis acid catalyst". experimental part. p. 83 - 90. Retrieved 2012/05/20.