ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside
• CAS No.: 138624-50-7
• Molecular Formula: C₂₁H₂₈O₈S
• Molecular Weight: 440.515
• Mol file: 138624-50-7.mol

Synonyms:ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside

Chemical Property of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside

There total 5 articles about ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-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: 93.0%

acetic anhydride (108-24-7) + ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside (173987-57-0) → ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside (138624-50-7)

Guidance literature:

With pyridine; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(95)00269-3

Reference yield:

(ethylthio)trimethylsilane (5573-62-6) + 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α- and β-D-glucopyranose (72984-63-5) → ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside (138624-50-7) + ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 16h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/S0040-4020(97)00307-4

Reference yield:

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (29741-69-3) → ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-deoxy-1-ethylthio-β-D-glucopyranoside (138624-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MeONa / methanol / 1 h / 20 °C

2: pyridine / 12 h

With pyridine; sodium methylate; In methanol;

upstream raw materials:

acetic anhydride

ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide

ethanethiol

Downstream raw materials:

ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside

2-(4-trifluoroacetamidophenyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside

methyl <2-(4-trifluoroacetamidophenyl)ethyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-5-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-manno-oct-2-ulopyranosid>onate

2-(4-trifluoroacetamidophenyl)ethyl 2-O-benzyl-α-D-glucopyranoside