11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• CAS No.: 578730-55-9
• Molecular Formula: C₄₄H₄₆O₁₄S
• Molecular Weight: 830.907
• Mol file: 578730-55-9.mol

Synonyms:11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Chemical Property of 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

There total 7 articles about 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 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: 75.0%

2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (151767-11-2) + S-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)thioacetate (223611-42-5,165729-83-9) → 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (578730-55-9)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1002/chem.200204544

Reference yield:

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (578730-55-9)

Guidance literature:

Multi-step reaction with 3 steps

1: AcO(-)N₂H₅(+) / dimethylformamide / 60 °C

2: DBU / CH₂Cl₂ / 2 h

3: 75 percent / TMSOTf / CH₂Cl₂ / 0.25 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.200204544

Reference yield:

2,3,4,6-tetra-O-benzoyl-D-glucopyranose (627466-64-2) → 11-thioacetyl-3,6,9-trioxaundecanyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside (578730-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 2 h

2: 75 percent / TMSOTf / CH₂Cl₂ / 0.25 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1002/chem.200204544

upstream raw materials:

2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

S-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)thioacetate

1,2,3,4,6-penta-O-benzoyl-D-glucopyranoside

Tetraethylene glycol