(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

Base Information

Chemical Name:(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate
CAS No.:1585232-69-4
Molecular Formula:C₆₂H₉₉NO₁₂
Molecular Weight:1050.47
Hs Code.:

Synonyms:(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

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Chemical Property of (2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

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Technology Process of (2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

There total 8 articles about (2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate 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:

: 1585232-52-5
phenyl 6-O-{3-[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

: 1585232-69-4
(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

: 1585232-67-2
C₆₂H₉₉NO₁₂

Guidance literature:: With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; acetonitrile; at 0 ℃; for 2h; Solvent; Overall yield = 77 %; Overall yield = 33 mg; Molecular sieve; Inert atmosphere;
DOI:10.3390/molecules181215153

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 1585232-69-4
(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

: 1585232-67-2
C₆₂H₉₉NO₁₂

Guidance literature:: Multi-step reaction with 6 steps

1.1: (1S)-10-camphorsulfonic acid / acetonitrile; N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 17 h / 20 °C / Inert atmosphere

3.1: acetic acid / water / 1.5 h / 50 °C / Inert atmosphere

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

5.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6.1: dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate / acetonitrile; dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3390/molecules181215153

Reference yield:

: 1046791-67-6
(2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-succinoyl-2-octadecanamido-4-octadecene-1,3-diol

: 1585232-69-4
(2,3-di-O-p-methoxybenzyl-β-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-succinate

: 1585232-67-2
C₆₂H₉₉NO₁₂

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3: dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate / acetonitrile; dichloromethane / 2 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.3390/molecules181215153