beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate

Base Information

• Chemical Name: beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate
• CAS No.: 438-95-9
• Molecular Formula: C₁₉H₂₄FNO₉S
• Molecular Weight: 461.465
• DSSTox Substance ID: DTXSID601121154
• Mol file: 438-95-9.mol

Synonyms:DTXSID601121154;438-95-9;beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate

Chemical Property of beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 461.11558068
• Heavy Atom Count: 31
• Complexity: 761

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC2C(C(C(OC2F)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2F)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate

There total 2 articles about beta-D-Glucopyranosyl fluoride, 2-deoxy-2-[[(4-methylphenyl)sulfonyl]amino]-, 3,4,6-triacetate 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:

3,4,6-tri-O-acetyl-2-deoxy-2-p-toluenesulfonamido-α-D-glucopyranosyl bromide (78151-17-4) → tri-O-acetyl-2-(toluene-4-sulfonylamino)-2-deoxy-β-D-glucopyranosyl fluoride (438-95-9)

Guidance literature:

With silver fluoride; acetonitrile;

Reference yield:

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (7772-82-9) → tri-O-acetyl-2-(toluene-4-sulfonylamino)-2-deoxy-β-D-glucopyranosyl fluoride (438-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen bromide

2: acetonitrile; silver fluoride

With hydrogen bromide; silver fluoride; acetonitrile;

Reference yield:

tri-O-acetyl-2-(toluene-4-sulfonylamino)-2-deoxy-β-D-glucopyranosyl fluoride (438-95-9) → 2-(toluene-4-sulfonylamino)-1,6-anhydro-2-deoxy-β-D-glucopyranose (109097-15-6)

Guidance literature:

With methanol; sodium methylate;

upstream raw materials:

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

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Downstream raw materials:

tri-O-acetyl-2-[methyl-(toluene-4-sulfonyl)-amino]-2-deoxy-β-D-glucopyranosyl fluoride

2-(toluene-4-sulfonylamino)-1,6-anhydro-2-deoxy-β-D-glucopyranose

O³,O⁴-diacetyl-2-(toluene-4-sulfonylamino)-1,6-anhydro-2-deoxy-β-D-glucopyranose

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