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

Base Information

Chemical Name:O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester
CAS No.:370554-14-6
Molecular Formula:C₃₈H₃₈N₄O₉
Molecular Weight:694.741
Hs Code.:

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

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

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

There total 4 articles about O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-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: 81.0%

: 21209-51-8
N-benzyloxycarbonyl-L-serine benzyl ester

: 370554-13-5
phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-galactopyranoside

: O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester

: 370554-14-6
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: With N-iodo-succinimide; silver trifluoromethanesulfonate; trityl chloride; 5A molecular sieve; In toluene; at -35 ℃; for 1.5h;
DOI:10.1246/bcsj.76.1829

Reference yield:

: 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-galactopyranose

: 370554-14-6
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: SOCl₂; DMF / CH₂Cl₂ / 12 h / 20 °C

2: NaH / tetrahydrofuran; various solvent(s) / 3 h / 20 °C

3: 81 percent / Ph₃CCl; AgOTf; N-iodsuccinimide / molecular sieves 5 Angstroem / toluene / 1.5 h / -35 °C

With N-iodo-succinimide; thionyl chloride; silver trifluoromethanesulfonate; trityl chloride; sodium hydride; N,N-dimethyl-formamide; 5A molecular sieve; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1246/bcsj.76.1829

Reference yield:

: 625388-51-4
(2S,4aR,7R,8R,8aR)-7-Azido-8-benzyloxy-6-chloro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 370554-14-6
O-(2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran; various solvent(s) / 3 h / 20 °C

2: 81 percent / Ph₃CCl; AgOTf; N-iodsuccinimide / molecular sieves 5 Angstroem / toluene / 1.5 h / -35 °C

With N-iodo-succinimide; silver trifluoromethanesulfonate; trityl chloride; sodium hydride; 5A molecular sieve; In tetrahydrofuran; toluene;
DOI:10.1246/bcsj.76.1829