HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 115414-47-6
• Molecular Formula: C₃₀H₅₃NO₉
• Molecular Weight: 571.752
• Mol file: 115414-47-6.mol

Synonyms:HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Hexadecyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-SS-D-GLUCOPYRANOSIDE

Chemical Property of HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• Boiling Point: 656.1±55.0 °C(Predicted)
• PKA: 13.61±0.70(Predicted)
• PSA: 126.46000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 5.53130

Purity/Quality:

98% ^*data from raw suppliers

HEXADECYL-2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of HEXADECYL 2-ACETAMIDO-3,4,6-TRI-O-ACETYL-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

There total 2 articles about HEXADECYL 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-Hexadecanol (36653-82-4,124-29-8) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → hexadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (115414-47-6)

Guidance literature:

With trityl chloride; zinc(II) chloride; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4039(00)75823-0

Reference yield: 70.0%

1-Hexadecanol (36653-82-4,124-29-8) + 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) → hexadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (115414-47-6)

Guidance literature:

With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; Heating;

DOI:10.1007/BF00598682

Reference yield: 98.0%

hexadecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (115414-47-6) → hexadecyl 2-acetamido-2-deoxy-β-D-glucopyranoside (115414-49-8)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 1h;

DOI:10.1007/BF00598682

upstream raw materials:

1-Hexadecanol

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

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

Downstream raw materials:

hexadecyl 2-acetamido-2-deoxy-β-D-glucopyranoside

hexadecyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

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

hexadecyl 2-acetamido-4,6-O-benzylidene-3-O-(D-1-carboxyethyl)-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Kumar, Erukulla Ravi,Byun, Hoe-Sup,Wang, Sihe,Bittman, Robert. "Preparation of ether-linked 2-acetamido-2-deoxy β-glycolipids via zinc chloride promoted coupling of Ac4GlcNAc-CI with lipid hydroxy groups". . p. 505 - 508. Retrieved 1994.
• 2、 Zemyakov, A. E.,Chirva, V. Ya.. "SYNTHESIS OF GLYCOSIDIC ANALOGUES OF N-ACETYLNEURAMOYL-L-ALANYL-D-ISOGLUTAMINE". . p. 595 - 599. Retrieved 2007/10/02.