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

Base Information

Chemical Name:phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside
CAS No.:1585232-50-3
Molecular Formula:C₇₄H₁₁₉NO₁₂SSi
Molecular Weight:1274.91
Hs Code.:

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

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

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Chemical Property of phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

There total 3 articles about phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-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: 70.0%

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

: 1046791-11-0
phenyl 2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

: 1585232-50-3
phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.3390/molecules181215153

Reference yield:

: 1215008-40-4
(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-1,3-diol

: 1585232-50-3
phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C

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

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;
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

: 1585232-50-3
phenyl 6-O-{3-[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylpropanoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

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