ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE

Base Information

• Chemical Name: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE
• CAS No.: 41670-79-5
• Molecular Formula: C₁₆H₂₄O₉S
• Molecular Weight: 392.427
• Mol file: 41670-79-5.mol

Synonyms:Ethyl2,3,4,6-tetra-O-acetyl-1-thio-a-D-glucopyranoside

Chemical Property of ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE

Chemical Property:

• PSA: 139.73000
• LogP: 0.82260
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 2,3,4,6-Tetra-O-acetyl-b-D-thioglucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE is a useful reagent for the preparation of glucosides Ethyl 2,3,4,6-Tetra-O-acetyl-α-D-thioglucopyranoside is a useful reagent in the preparation of glycosides.

Technology Process of ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE

There total 72 articles about ETHYL 2,3,4,6-TETRA-O-ACETYL-A-D-THIOGLUCOPYRANOSIDE 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%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (127753-95-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; at -10 ℃;

DOI:10.1039/a909218h

Reference yield: 96.0%

acetyl chloride (75-36-5) + 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-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 92.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) + ethanethiol (75-08-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

D-Glucose; acetic anhydride; With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

ethanethiol; With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200500646

upstream raw materials:

ethanethiol

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

tri-n-butyltin(SC₂H₅)

Downstream raw materials:

ethyl 1-thio-α-D-mannopyranoside

8-azidooctyl 5-O-{3,4,6-tri-O-benzyl-2-O-[3,4,6-tri-O-benzyl-2-O-(α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranosyl}-2,3-di-O-benzyl-β-D-arabinofuranoside

ethyl 4,6-di-O-benzyl-2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

ethyl 4,6-di-O-benzyl-1-thio-α-D-mannopyranoside

Refernces

• 1、 -. "Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof". Paragraph 0033; 0057; 0059. . Retrieved 2021/04/03.
• 2、 Bavaro, Teodora,Marzatico, Sara,Recca, Teresa,Robescu, Marina Simona,Tanzi, Lisa,Terreni, Marco,Zhang, Yongmin. "Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks". . . Retrieved 2021/06/14.