1,3,4,6-Tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose
• CAS No.: 63301-57-5
• Molecular Formula: C21H27NO11S
• Molecular Weight: 501.5042
• NSC Number: 108106
• DSSTox Substance ID: DTXSID90296172
• Mol file: 63301-57-5.mol

Synonyms:63301-57-5;1,3,4,6-tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose;NSC108106;DTXSID90296172;NSC-108106

Chemical Property of 1,3,4,6-Tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose

Chemical Property:

• Vapor Pressure: 2.87E-14mmHg at 25°C
• Boiling Point: 598.1°Cat760mmHg
• Flash Point: 315.5°C
• Density: 1.37g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 12
• Exact Mass: 501.13048185
• Heavy Atom Count: 34
• Complexity: 860

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC2C(C(C(OC2OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1,3,4,6-Tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose

There total 5 articles about 1,3,4,6-Tetra-o-acetyl-2-deoxy-2-{[(4-methylphenyl)sulfonyl]amino}hexopyranose 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:

[bis(acetoxy)iodo]benzene (3240-34-4) + toluene-4-sulfonamide (70-55-3) + D-glucal triacetate (2873-29-2) → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (7772-82-9) + 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(p-toluenesulfonyl)amido-α-D-glucopyranose (63301-57-5)

Guidance literature:

toluene-4-sulfonamide; D-glucal triacetate; With tetrakis(μ-trifluoroacetamidato)dirhodium(II); magnesium oxide; In chlorobenzene; Inert atmosphere;

[bis(acetoxy)iodo]benzene; In chlorobenzene; at 5 - 20 ℃; for 12h; Overall yield = 25 %; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2016.09.001

Reference yield:

2-deoxy-2-p-toluenesulfonamido-D-glucose (78138-84-8) + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(p-toluenesulfonyl)amido-α-D-glucopyranose (63301-57-5)

Guidance literature:

With pyridine; for 4h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85251-9

Reference yield:

→ 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(p-toluenesulfonyl)amido-α-D-glucopyranose (63301-57-5)

Guidance literature:

With pyridine; acetic anhydride;

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrobromide

p-toluenesulfonyl chloride

2-deoxy-2-p-toluenesulfonamido-D-glucose

acetic anhydride

Downstream raw materials:

tri-O-acetyl-2-(toluene-4-sulfonylamino)-2-deoxy-α-D-glucopyranosyl fluoride

tetra-O-acetyl-2-[methyl-(toluene-4-sulfonyl)-amino]-2-deoxy-α-D-glucopyranose

N-(O¹-methyl-α-D-glucopyranose-2-yl)-toluene-4-sulfonamide

3,4,6-tri-O-acetyl-2-deoxy-2-p-toluenesulfonamido-α-D-glucopyranosyl bromide