2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
• CAS No.: 453524-99-7
• Molecular Formula: C₃₆H₂₈Cl₃NO₉S
• Molecular Weight: 757.045
• Mol file: 453524-99-7.mol

Synonyms:2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

There total 5 articles about 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate 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: 72.0%

trichloroacetonitrile (545-06-2) + 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranose (453525-17-2) → 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate (453524-99-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 0 ℃;

DOI:10.1246/cl.2002.626

Reference yield:

tetrahydropyran-2-yl 2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranoside (453525-11-6) → 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate (453524-99-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / NaOMe / methanol / 3.5 h / 20 °C

2: 94 percent / pyridine / 1 h / 20 °C

3: 85 percent / p-TsOH / methanol / 7 h / 45 °C

4: 67 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2005.05.028

Reference yield:

tetrahydropyran-2-yl 5-deoxy-5-thio-α-D-glucopyranoside (453524-96-4) → 2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate (453524-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine / 1 h / 20 °C

2: 85 percent / p-TsOH / methanol / 7 h / 45 °C

3: 67 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2005.05.028

upstream raw materials:

trichloroacetonitrile

2,3,4,6-tetra-O-benzoyl-5-deoxy-5-thio-α-D-glucopyranose

2,3,4,6-Tetra-O-acetyl-5-thio-α-D-glucopyranose

tetrahydropyran-2-yl 5-deoxy-5-thio-α-D-glucopyranoside

Downstream raw materials:

4-nitrophenyl 2,3,4-tri-O-benzoyl-6-O-[2',3',4',6'-tetra-O-benzoyl-5'-deoxy-5'-thio-D-glucopyranosyl]-α-D-glucopyranoside

C₆₂H₅₂O₁₇S

methyl 6-O-[2',3',4',6'-tetra-O-benzoyl-5'-deoxy-5'-thio-D-glucopyranosyl]-2,3,4-tri-O-benzoyl-α-D-glucopyranoside