b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate

Base Information

• Chemical Name: b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate
• CAS No.: 113214-71-4
• Molecular Formula: C36H32O9S
• Molecular Weight: 640.69900
• Hs Code.: 2932990090
• Mol file: 113214-71-4.mol

Synonyms:ethyl 1-thio-b-D-glucopyranoside,2,3,4,6-tetrabenzoate;

Chemical Property of b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate

Chemical Property:

• PSA: 139.73000
• LogP: 5.99820

Purity/Quality:

99.3% ^*data from raw suppliers

(2R,3R,4S,5R,6S)-2-((Benzoyloxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triylTribenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2R,3R,4S,5R,6S)-2-((Benzoyloxy)methyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triyl Tribenzoate is used as a reactant in the synthesis of oligosaccharides.

Technology Process of b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate

There total 20 articles about b-D-Glucopyranoside, ethyl 1-thio-, 2,3,4,6-tetrabenzoate 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: 100.0%

benzoyl chloride (98-88-4) + ethyl 1-thio-β-D-galactopyranoside (56245-60-4,686299-00-3) → ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside (105376-04-3,113214-71-4,138661-53-7)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 12h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201900143

Reference yield: 92.0%

benzoyl chloride (98-88-4) + ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside (105376-04-3,138661-53-7,113214-71-4)

Guidance literature:

With pyridine; at 20 ℃; for 16h;

DOI:10.1016/S0040-4020(01)87208-2

Reference yield: 83.0%

1,2,3,4,6-penta-O-benzoyl-β-D-galactopyranose (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) + ethanethiol (75-08-1) → ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside (105376-04-3,113214-71-4,138661-53-7)

Guidance literature:

With 4 Angstroem MS; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1080/07328309808002341

upstream raw materials:

ethylmagnesium bromide

2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl thiocyanate

benzoyl chloride

ethyl 1-thio-β-D-glucopyranoside

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside

C₅₅H₅₂O₁₄

C₄₈H₅₀O₁₆

C₅₃H₅₆O₁₈

Refernces

• 1、 Krumb, Matthias,Lucas, Tobias,Opatz, Till. "Visible Light Enables Aerobic Iodine Catalyzed Glycosylation". supporting information. p. 4517 - 4521. Retrieved 2019/08/06.
• 2、 -. "SYNTHESIS OF AMPHIPHILIC CALIXARENE GLYCOSIDE DETERGENTS AND USE OF SAME FOR EXTRACTING AND STABILIZING NATIVE FUNCTIONAL MEMBRANE PROTEINS". Page/Page column 18. . Retrieved 2015/11/09.