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

Base Information

• Chemical Name: (2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-(o-hydroxycarbonylbenzoate)-2-octadecanamido-4-octadecene-1,3-diol
• CAS No.: 1585232-47-8
• Molecular Formula: C₅₀H₈₉NO₆Si
• Molecular Weight: 828.345
• Mol file: 1585232-47-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-(o-hydroxycarbonylbenzoate)-2-octadecanamido-4-octadecene-1,3-diol 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: 100.0%

phthalic anhydride (85-44-9) + (2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-1,3-diol (1215008-40-4) → (2S,3R,4E)-1-O-tert-butyldimethylsilyl-3-O-(o-hydroxycarbonylbenzoate)-2-octadecanamido-4-octadecene-1,3-diol (1585232-47-8)

Guidance literature:

With pyridine; dmap; triethylamine; at 0 - 40 ℃; for 23h; Inert atmosphere;

DOI:10.3390/molecules181215153

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:

(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)-2-octadecanamido-4-octadecene-3-yloxy-1,3-diol]carbonylbenzoyl}-2,3-di-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside (1585232-66-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.3390/molecules181215153

upstream raw materials:

phthalic anhydride

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

Downstream raw materials:

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

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