2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride

Base Information

• Chemical Name: 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride
• CAS No.: 187330-17-2
• Molecular Formula: C₁₅H₁₅ClFN₃O₅
• Molecular Weight: 371.753
• Mol file: 187330-17-2.mol

Synonyms:2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride

Chemical Property of 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride

There total 1 articles about 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride 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: 52.0%

(2S,4aR,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol (186972-18-9) + Chloroacetic anhydride (541-88-8) → 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride (187330-17-2) + 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl fluoride (187330-16-1)

Guidance literature:

With pyridine; dmap; In 1,2-dichloro-ethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0968-0896(96)00172-1

Reference yield: 79.0%

N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester (136497-85-3) + 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride (187330-17-2) → N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl)-L-serine allyl ester + N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-serine allyl ester (187330-18-3)

Guidance literature:

With zirconocene dichloride; 4 A molecular sieve; silver perchlorate; In 1,2-dichloro-ethane; at -25 - 5 ℃; for 5h;

DOI:10.1016/S0968-0896(96)00172-1

Reference yield:

2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-galactopyranosyl fluoride (187330-17-2) → C55H64N4O20 (187330-21-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / Cp₂ZrCl₂, AgClO₄, mol. sieves 4A / 1,2-dichloro-ethane / 5 h / -25 - 5 °C

2: 74 percent / thiourea / dimethylformamide / 0.75 h / 90 °C

3: 68 percent / CuBr₂, AgOTf, n-Bu₄NBr, mol. sieves 4A / 1,2-dichloro-ethane / 3 h / Ambient temperature

4: 82 percent / 80percent aq. CF₃CO₂H / CH₂Cl₂ / 1.5 h / 0 °C

With zirconocene dichloride; 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; silver perchlorate; thiourea; trifluoroacetic acid; copper(ll) bromide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(96)00172-1

upstream raw materials:

(2S,4aR,7R,8R,8aR)-7-Azido-6-fluoro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Chloroacetic anhydride

Downstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-serine allyl ester

allyl N-(9-fluorenylmethoxycarbonyl)-[O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-(1[*]3)]-L-serine

C₅₅H₆₄N₄O₂₀

C₆₂H₆₈N₄O₂₀