ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside
CAS No.:1276031-17-4
Molecular Formula:C₂₄H₃₃NO₁₀
Molecular Weight:495.527
Hs Code.:

Synonyms:ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

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Chemical Property of ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

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Technology Process of ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

There total 7 articles about ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside 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: 31.0%

: 64-17-5
ethanol

: 1276031-15-2
p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-1-thio-β-D-glucopyranoside

: 1276031-17-4
ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; 2,4,6-tri-tertbutylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 10 - 20 ℃; Molecular sieve;
DOI:10.1016/j.carres.2010.11.026

Reference yield:

: 1276031-13-0
p-methylphenyl 2-deoxy-2-(4-methoxybenzylamino)-1-thio-β-D-glucopyranoside

: 1276031-17-4
ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 12 h / 20 °C / Inert atmosphere

2: N-iodo-succinimide; 2,4,6-tri-tertbutylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 10 - 20 °C / Molecular sieve

With pyridine; N-iodo-succinimide; 2,4,6-tri-tertbutylpyridine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1016/j.carres.2010.11.026

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 1276031-17-4
ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-[acetyl(4-methoxybenzyl)amino]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0 - 20 °C

2: hydrazine hydrate / methanol / 12 h / Reflux; Inert atmosphere

3: tetrahydrofuran / 2 h / Reflux

4: triacetoxyborane / methanol / 12 h / 20 °C / Inert atmosphere

5: pyridine / 12 h / 20 °C / Inert atmosphere

6: N-iodo-succinimide; 2,4,6-tri-tertbutylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 10 - 20 °C / Molecular sieve

With pyridine; N-iodo-succinimide; 2,4,6-tri-tertbutylpyridine; triacetoxyborane; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrazine hydrate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.carres.2010.11.026