N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

Base Information

Chemical Name:N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester
CAS No.:875484-88-1
Molecular Formula:C₅₀H₅₆N₄O₁₉
Molecular Weight:1017.01
Hs Code.:

N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

Synonyms:N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

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Chemical Property of N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

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Technology Process of N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

There total 3 articles about N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester 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: 56.0%

: 875484-87-0
4-methylphenyl-2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside

: 125760-27-2
N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester

: N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranosyl]-L-threonine phenacylester

: 875484-88-1
N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

Guidance literature:: With 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In diethyl ether; dichloromethane; toluene; at 20 ℃; for 5h;
DOI:10.1016/j.carres.2005.11.010

Reference yield:

: 875484-86-9
4-methylphenyl 2-azido-3,4-O-isopropylidene-2-deoxy-1-thio-β-D-galactopyranoside

: 875484-88-1
N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / 4 Angstroem molecular sieves; silver triflate / toluene; CH₂Cl₂ / -40 - -30 °C

2: 56 percent / 4 Angstroem molecular sieves; DMTST / CH₂Cl₂; diethyl ether; toluene / 5 h / 20 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In diethyl ether; dichloromethane; toluene;
DOI:10.1016/j.carres.2005.11.010

Reference yield:

: 125760-22-7
p-methylphenyl 2-deoxy-2-azido-1-thio-β-D-galactopyranoside

: 875484-88-1
N-(9-fluorenylmethyloxycarbonyl)-O-[2-azido-3,4-O-isopropylidene-2-deoxy-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine phenacylester

Guidance literature:: Multi-step reaction with 3 steps

1: 39 percent / TsOH / acetonitrile / 2 h

2: 86 percent / 4 Angstroem molecular sieves; silver triflate / toluene; CH₂Cl₂ / -40 - -30 °C

3: 56 percent / 4 Angstroem molecular sieves; DMTST / CH₂Cl₂; diethyl ether; toluene / 5 h / 20 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.carres.2005.11.010