p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

Base Information

Chemical Name:p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside
CAS No.:1449491-94-4
Molecular Formula:C₂₂H₃₅NO₆Si
Molecular Weight:437.608
Hs Code.:

Synonyms:p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

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Chemical Property of p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

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Technology Process of p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

There total 8 articles about p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-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: 81.0%

: 1449491-93-3
p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-4-O-methyl-2-deoxy-2-azido-α-D-altropyranoside

: 108-24-7
acetic anhydride

: 1449491-94-4
p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

Guidance literature:: p-methoxyphenyl 6-O-(tert-butyldimethylsilyl)-4-O-methyl-2-deoxy-2-azido-α-D-altropyranoside; With triphenylphosphine; In toluene; at 0 ℃; for 12.3333h; Inert atmosphere; Reflux;

acetic anhydride; With pyridine; In toluene; at 0 ℃; for 0.666667h;
DOI:10.1016/j.tet.2013.07.018

Reference yield:

: C₂₁H₃₅N₃O₈SSi

: 108-24-7
acetic anhydride

: 1449491-94-4
p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

Guidance literature:: C₂₁H₃₅N₃O₈SSi; With triphenylphosphine; In acetonitrile; at 0 ℃; for 0.166667h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; for 15h; Inert atmosphere; Reflux;

acetic anhydride; With pyridine; In water; acetonitrile; at 0 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1016/j.tet.2013.07.018

Reference yield:

: 197449-36-8
p-methoxyphenyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

: 1449491-94-4
p-methoxyphenyl 2,3-(acetylepimino)-6-O-(tert-butyldimethylsilyl)-4-O-methyl-2,3-dideoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hydrogencarbonate; dihydrogen peroxide / acetonitrile / 4 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

3.1: silver(l) oxide / N,N-dimethyl-formamide / 23 h / 20 °C / Inert atmosphere

4.1: ammonium chloride; sodium azide / methanol; water / 72 h / 80 °C

5.1: triphenylphosphine / toluene / 12.33 h / 0 °C / Inert atmosphere; Reflux

5.2: 0.67 h / 0 °C

With 1H-imidazole; sodium azide; dihydrogen peroxide; ammonium chloride; potassium hydrogencarbonate; triphenylphosphine; silver(l) oxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.tet.2013.07.018