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

Base Information

Chemical Name:phenyl 6-O-{[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside
CAS No.:1585232-66-1
Molecular Formula:C₇₂H₁₀₅NO₁₂S
Molecular Weight:1208.69
Hs Code.:

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

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

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

There total 7 articles about phenyl 6-O-{[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-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: 90.0%

: 1585232-63-8
phenyl 6-O-{[(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

: 1585232-66-1
phenyl 6-O-{[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 4h; 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

: 1585232-66-1
phenyl 6-O-{[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 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 / 5.5 h / 0 - 20 °C / Inert atmosphere

5.1: acetic acid; dmap / tetrahydrofuran / 4 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 tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.3390/molecules181215153

Reference yield:

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

: 1585232-66-1
phenyl 6-O-{[(2S,3R,4E)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine; pyridine; dmap / 23 h / 0 - 40 °C / Inert atmosphere

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5.5 h / 0 - 20 °C / Inert atmosphere

3: acetic acid; dmap / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.3390/molecules181215153