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

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS No.: 7772-82-9
• Molecular Formula: C₂₁H₂₇NO₁₁S
• Molecular Weight: 501.511
• Mol file: 7772-82-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl 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: 82.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + p-toluenesulfonyl chloride (98-59-9) → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (7772-82-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 26h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b00003

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:

p-toluenesulfonyl chloride (98-59-9) + tetra-acetyl glucosamine (17460-45-6,23707-23-5,23739-93-7,23743-51-3,26108-75-8,59042-16-9,124516-07-0,124580-56-9) → (2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(4-methylphenylsulfonamido)tetrahydro-2H-pyran-2,4,5-triyl triacetate (7772-82-9)

Guidance literature:

With pyridine;

upstream raw materials:

p-toluenesulfonyl chloride

tetra-acetyl glucosamine

[bis(acetoxy)iodo]benzene

toluene-4-sulfonamide

Downstream raw materials:

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

phenyl-[tri-O-acetyl-2-(toluene-4-sulfonylamino)-2-deoxy-α-D-glucopyranoside]

3,4,6-tri-O-acetyl-2-deoxy-2-(p-toluenesulfonamido)-α-D-glucopyranose

2-methyl-3-p-tolylsulfonyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyrano)-<2,1-d>-1-imidazoline