1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose
• CAS No.: 634891-69-3
• Molecular Formula: C₁₅H₁₉ClO₇S
• Molecular Weight: 378.831
• Mol file: 634891-69-3.mol

Synonyms:1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose

Chemical Property of 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose

There total 1 articles about 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose 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: 87.0%

1,6:3,4-dianhydro-2-O-tosyl-D-galactose (6167-32-4) + 2-chloro-ethanol (107-07-3) → 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose (634891-69-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 40 ℃; for 4h;

DOI:10.1135/cccc20031295

Reference yield: 98.0%

acetic anhydride (108-24-7) + 1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose (634891-69-3) → 3-O-acetyl-1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose (634891-70-6)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1135/cccc20031295

Reference yield:

1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose (634891-69-3) → 3-acetamido-1,6-anhydro-3-deoxy-3-N,4-O-ethylene-2-O-tosyl-β-D-altropyranose

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / pyridine / 20 °C

2: 89 percent / NaN₃ / dimethylformamide / 3 h / 90 °C

3: H₂ / Pd/C / ethanol / 24 h / 20 °C

4: 94 percent / MeONa / methanol / 20 °C

5: 85 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / butan-1-ol / 2 h / 120 °C

6: 96 percent / AcONa / 0.5 h / 70 °C

7: 98 percent / MeONa / methanol / 1 h / 20 °C

8: 85 percent / pyridine / 20 °C

With pyridine; sodium azide; hydrogen; sodium methylate; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide; butan-1-ol;

DOI:10.1135/cccc20031295

upstream raw materials:

1,6:3,4-dianhydro-2-O-tosyl-D-galactose

2-chloro-ethanol

Downstream raw materials:

3-O-acetyl-1,6-anhydro-4-O-(2-chloroethyl)-2-O-tosyl-β-D-glucopyranose

3-O-acetyl-4-O-(2-aminoethyl)-1,6-anhydro-2-O-tosyl-β-D-glucopyranose

3-O-acetyl-1,6-anhydro-4-O-(2-azidoethyl)-2-O-tosyl-β-D-glucopyranose