N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine 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-threonine benzyl ester
CAS No.:282736-09-8
Molecular Formula:C₄₁H₃₉ClN₄O₁₀
Molecular Weight:783.234
Hs Code.:

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

There total 8 articles about N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine 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: 76.0%

: 73724-48-8
N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

: 282736-08-7
Phenyl 2-azido-4,6-benzylidene-3-O-chloroacetyl-2-deoxy-1-seleno-α-D-galactopyranoside

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

: 282736-09-8
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Guidance literature:: With silver trifluoromethanesulfonate; potassium carbonate; tetramethylurea; calcium sulfate; In dichloromethane; at -10 - 25 ℃; for 36h;
DOI:10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y

Reference yield:

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

: 73724-48-8
N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

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

: 282736-09-8
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Guidance literature:: With tetrahydrofuran; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; at -60 ℃; for 48h; optical yield given as %de; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1016/j.tet.2012.04.059

Reference yield:

: 862851-12-5
phenyl 2-azido-2-deoxy-1-seleno-α-D-galactopyranoside

: 282736-09-8
N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 19.4 g / p-TsOH / 3 h / 20 °C

2: 100 percent / NaHCO₃ / tetrahydrofuran / 20 °C

3: 76 percent / AgOTf; K₂CO₃; TMU / drierite / CH₂Cl₂ / 36 h / -10 - 25 °C

With silver trifluoromethanesulfonate; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; tetramethylurea; calcium sulfate; In tetrahydrofuran; dichloromethane;
DOI:10.1002/1521-3765(20010202)7:3<585::AID-CHEM585>3.3.CO;2-Y