Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside
• CAS No.: 211567-22-5
• Molecular Formula: C₂₆H₄₅NO₉
• Molecular Weight: 515.645
• DSSTox Substance ID: DTXSID101152067
• Mol file: 211567-22-5.mol

Synonyms:211567-22-5;Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside;(2R,3S,4R,5R,6R)-5-Acetamido-2-(acetoxymethyl)-6-(dodecyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate;[(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-(dodecyloxy)-5-acetamidooxan-2-yl]methyl acetate;Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;SCHEMBL20516521;DTXSID101152067;AKOS027282727;W-201867;Z1815149233;Dodecyl-2-(acetylamino)-2-deoxy-3,4,6-triacetateI(2)-D-Glucopyranoside;[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-dodecoxyoxan-2-yl]methyl acetate

Chemical Property of Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• Melting Point: 103-105℃ (ethyl ether )
• Boiling Point: 616.7±55.0 °C(Predicted)
• PKA: 13.61±0.70(Predicted)
• PSA: 126.46000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.97090
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 20
• Exact Mass: 515.30943201
• Heavy Atom Count: 36
• Complexity: 684

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCOC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Isomeric SMILES: CCCCCCCCCCCCO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C

Technology Process of Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

There total 4 articles about Dodecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-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: 82.0%

1-dodecyl alcohol (112-53-8) + 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (211567-22-5)

Guidance literature:

With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 85 - 90 ℃;

DOI:10.1134/S1068162006040091

Reference yield: 80.0%

1-Decanol (112-30-1) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (211567-22-5)

Guidance literature:

With silica-gel-supported sulfuric acid; In 1,2-dichloro-ethane; at 110 ℃; for 0.25h; stereoselective reaction; Microwave irradiation;

DOI:10.1055/s-0029-1218304

Reference yield: 63.8%

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9) + 1-dodecyl alcohol (112-53-8) → dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside (211567-22-5)

Guidance literature:

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 50 ℃; for 7h;

1-dodecyl alcohol; With 4 A molecular sieve; boron trifluoride diethyl etherate; at 20 ℃; for 22h; Further stages.;

DOI:10.1016/j.carres.2008.01.022

upstream raw materials:

1-dodecyl alcohol

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

Downstream raw materials:

dodecyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside

dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside

Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-dodecyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester