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

Base Information

• Chemical Name: Tetradecyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside
• CAS No.: 173725-25-2
• Molecular Formula: C₂₈H₄₉NO₉
• Molecular Weight: 543.698
• Mol file: 173725-25-2.mol

Synonyms:TETRADECYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-SS-D-GLUCOPYRANOSIDE; Tetradecyl2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-b-D-glucopyranoside;

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

Chemical Property:

• PSA: 126.46000
• LogP: 4.75110

Purity/Quality:

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

TETRADECYL-2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-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 Tetradecyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranoside

There total 4 articles about Tetradecyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-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: 80.0%

tetradecyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxysulfonyl)amido-β-D-glucopyranoside + acetic anhydride (108-24-7) → n-tetradecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-dlucopyranoside (173725-25-2)

Guidance literature:

With copper(II) sulfate; zinc; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c4ra02367f

Reference yield: 62.0%

1-Tetradecanol (112-72-1) + 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) → n-tetradecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-dlucopyranoside (173725-25-2)

Guidance literature:

With 4 A molecular sieve; iron(III) chloride; In dichloromethane; for 10h; Heating;

DOI:10.1016/0008-6215(95)00229-1

Reference yield:

D-glucal triacetate (2873-29-2) → n-tetradecyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-dlucopyranoside (173725-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(μ-trifluoroacetamidato)dirhodium(II); iodosylbenzene / chlorobenzene / 1 h / 5 °C / Molecular sieve

2: zinc; copper(II) sulfate / tetrahydrofuran / 20 °C

With tetrakis(μ-trifluoroacetamidato)dirhodium(II); iodosylbenzene; copper(II) sulfate; zinc; In tetrahydrofuran; chlorobenzene;

DOI:10.1039/c4ra02367f

upstream raw materials:

1-Tetradecanol

2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose

D-glucal triacetate

acetic anhydride

Downstream raw materials:

n-tetradecyl 2-acetamido-2-deoxy-β-D-glucopyranoside

Refernces

• 1、 Murakami, Teiichi,Sato, Yukari,Yoshioka, Kyoko,Tanaka, Mutsuo. "Convenient stereocontrolled amidoglycosylation of alcohols with acetylated glycals and trichloroethoxysulfonamide". . p. 121 - 131. Retrieved 2016/09/23.