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

Base Information

Chemical Name:N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester
CAS No.:1381864-56-7
Molecular Formula:C₄₀H₃₇ClN₄O₁₀
Molecular Weight:769.208
Hs Code.:

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

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

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

There total 2 articles about N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester 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:

: 1381864-50-1
2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl diphenyl phosphate

: 118358-66-0,73724-46-6
N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

: 1381864-57-8
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-β-D-galactopyranosyl)-L-serine benzyl ester

: 1381864-56-7
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

Guidance literature:: With tetrahydrofuran; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -40 ℃; for 6h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tet.2012.04.059

Reference yield:

: 2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-D-galactopyranose

: 1381864-57-8
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-β-D-galactopyranosyl)-L-serine benzyl ester

: 1381864-56-7
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1-methyl-1H-imidazole; triethylamine / toluene / 0.08 h / 0 °C / Inert atmosphere

2: tetrahydrofuran; trimethylsilyl trifluoromethanesulfonate / diethyl ether / 6 h / -40 °C / Inert atmosphere; Molecular sieve

With tetrahydrofuran; 1-methyl-1H-imidazole; trimethylsilyl trifluoromethanesulfonate; triethylamine; In diethyl ether; toluene;
DOI:10.1016/j.tet.2012.04.059

Reference yield: 88.0%

: 1381864-56-7
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

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

Guidance literature:: With sodium hydrogencarbonate; thiourea; In methanol; dichloromethane; at 20 ℃; for 8h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.04.059