ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside
• CAS No.: 1334525-90-4
• Molecular Formula: C₁₆H₁₈F₃N₃O₆S₂
• Molecular Weight: 469.463
• Mol file: 1334525-90-4.mol

Synonyms:ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside

There total 8 articles about ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-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: 99.0%

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside + trifluoromethylsulfonic anhydride (358-23-6) → ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside (1334525-90-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1016/j.carres.2011.05.024

Reference yield:

2-deoxy-2-amino glucose (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside (1334525-90-4)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium hydroxide / water / 24 h / 20 °C

2: pyridine

3: boron trifluoride diethyl etherate / chloroform / Reflux

4: methanol; sodium methylate

5: ethylenediamine / ethanol; toluene / Reflux

6: dmap; triflic azide / methanol; dichloromethane / 12 h / 20 °C

7: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

8: pyridine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; methanol; dmap; triflic azide; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ethylenediamine; sodium hydroxide; In methanol; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.carres.2011.05.024

Reference yield:

2-deoxy-2-phthalimido-D-glucopyranose (31505-45-0) → ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside (1334525-90-4)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine

2: boron trifluoride diethyl etherate / chloroform / Reflux

3: methanol; sodium methylate

4: ethylenediamine / ethanol; toluene / Reflux

5: dmap; triflic azide / methanol; dichloromethane / 12 h / 20 °C

6: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C

7: pyridine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; methanol; dmap; triflic azide; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ethylenediamine; In methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.carres.2011.05.024

upstream raw materials:

trifluoromethylsulfonic anhydride

2-deoxy-2-amino glucose

2-deoxy-2-phthalimido-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

Downstream raw materials:

ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside

ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside

ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside