Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 189758-87-0
• Molecular Formula: C₁₅H₂₁N₃O₈S
• Molecular Weight: 403.413
• Mol file: 189758-87-0.mol

Synonyms:Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester

There total 3 articles about Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester 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: 73.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3R,4S,5S,6R)-2-(2-Azido-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (165331-08-8) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (189758-87-0)

Guidance literature:

With pyridine; for 22h;

DOI:10.1002/chem.19970030318

Reference yield:

2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (140428-81-5) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (189758-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOMe / methanol / 0.42 h / Ambient temperature

2: 73 percent / pyridine / 22 h

With pyridine; sodium methylate; In methanol;

DOI:10.1002/chem.19970030318

Reference yield:

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (16977-77-8) → Toluene-4-sulfonic acid (2R,3S,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester (189758-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / NaN₃, KI / dimethylformamide / 1 h / Heating

2: 100 percent / NaOMe / methanol / 0.42 h / Ambient temperature

3: 73 percent / pyridine / 22 h

With pyridine; sodium azide; sodium methylate; potassium iodide; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/chem.19970030318

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3R,4S,5S,6R)-2-(2-Azido-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

2-azidoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

(2-chloroethyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3R,4S,5R,6R)-6-(2-azido-ethoxy)-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester