6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide

Base Information

• Chemical Name: 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide
• CAS No.: 438194-50-4
• Molecular Formula: C₄₀H₅₀F₃N₃O₁₈S
• Molecular Weight: 949.908
• Mol file: 438194-50-4.mol

Synonyms:6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide

Chemical Property of 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide

There total 5 articles about 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide 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:

chloroformic acid ethyl ester (541-41-3) + m-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline (130973-96-5) + 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid (438194-49-1) → 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide (438194-50-4)

Guidance literature:

chloroformic acid ethyl ester; 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid; With triethylamine; In DMF (N,N-dimethyl-formamide); at -60 ℃; for 0.5h; Cooling with acetone-dry ice;

m-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline; In DMF (N,N-dimethyl-formamide); at -60 - 20 ℃; for 5.58333h;

Reference yield:

m-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline (130973-96-5) + 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid (438194-49-1) → 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide (438194-50-4)

Guidance literature:

6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid; With chloroformic acid ethyl ester; triethylamine; In N,N-dimethyl-formamide; at -60 ℃; for 0.5h;

m-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline; In N,N-dimethyl-formamide; at 20 ℃; for 5.58333h;

DOI:10.1016/S0968-0896(01)00172-9

Reference yield:

hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) → 6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide (438194-50-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: thiourea; 48 percent hydrobromic acid / 9 h / 120 °C

1.2: 3.76 g / aq. NaOH / 3 h / 100 °C

2.1: 67 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

3.1: ethyl chloroformate; Et₃N / dimethylformamide / 0.5 h / -60 °C

3.2: 71 mg / dimethylformamide / 5.58 h / 20 °C

With boron trifluoride diethyl etherate; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; thiourea; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00172-9

upstream raw materials:

m-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline

6-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-triacetyl-β-D-glucopyranosylsulfanyl)hexanoic acid

hexahydro-2H-oxepin-2-one

6-mercaptocaproic acid

Downstream raw materials:

6-(β-D-galactopyranosyl-(1->4)-β-D-glucopyranosylsulfanyl)hexanoic acid [3-(3-fluoromethyl-3H-diazirin-3-yl)phenyl]amide