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

Base Information

• Chemical Name: 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
• CAS No.: 1585232-63-8
• Molecular Formula: C₇₈H₁₁₉NO₁₂SSi
• Molecular Weight: 1322.95
• Mol file: 1585232-63-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 5 articles about 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 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: 32.0%

phenyl 2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (1046791-11-0) + (2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-(o-hydroxycarbonylbenzoate)-2-octadecanamido-4-octadecene-1,3-diol (1585232-47-8) → 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 (1585232-63-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 5.5h; Inert atmosphere;

DOI:10.3390/molecules181215153

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (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) → 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 (1585232-63-8)

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 / 5.5 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

Reference yield:

(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-1,3-diol (1215008-40-4) → 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 (1585232-63-8)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.3390/molecules181215153

upstream raw materials:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

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

phenyl 2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

(2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-(o-hydroxycarbonylbenzoate)-2-octadecanamido-4-octadecene-1,3-diol

Downstream raw materials:

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

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

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