Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside

Base Information

• Chemical Name: Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside
• CAS No.: 28738-44-5
• Molecular Formula: C₁₇H₂₅NO₉
• Molecular Weight: 387.387
• Mol file: 28738-44-5.mol

Synonyms:Glucopyranoside,allyl 2-acetamido-2-deoxy-, 3,4,6-triacetate, β-D- (8CI);β-D-Glucopyranoside, 2-propenyl2-(acetylamino)-2-deoxy-, 3,4,6-triacetate (9CI);Allyl2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside;

Chemical Property of Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 151-157°C (dec.)
• Refractive Index: 1.492
• Boiling Point: 531.336 °C at 760 mmHg
• PKA: 13.67±0.70(Predicted)
• Flash Point: 275.142 °C
• PSA: 126.46000
• Density: 1.233 g/cm³
• LogP: 0.23600
• Storage Temp.: Refrigerator
• Solubility.: MethanolMethanol

Purity/Quality:

98% ^*data from raw suppliers

Allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--D-glucopyranoside

There total 37 articles about Allyl 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy--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: 98.0%

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) + acetic anhydride (108-24-7) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/j.bmc.2004.01.013

Reference yield: 85.0%

allyl alcohol (107-18-6) + acetic acid (3aR,5R,6R,7R,7aR)-6-acetoxy-5-acetoxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazol-7-yl ester (10378-06-0) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranoside (28738-44-5,63064-48-2,117299-90-8,126778-02-7,116288-58-5)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 70 ℃; for 4h; Molecular sieve; Sealed tube;

DOI:10.1055/s-0036-1591082

Reference yield: 84.0%

allyl alcohol (107-18-6) + 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) → allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (63064-48-2,116288-58-5,117299-90-8,126778-02-7,28738-44-5)

Guidance literature:

With camphor-10-sulfonic acid; In benzene; Heating; azeotropic removal of acetic acid;

DOI:10.1016/0040-4039(95)02233-3

upstream raw materials:

acetic anhydride

3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide

allyl alcohol

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

Downstream raw materials:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranose

3-benzylthiopropyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside