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

Base Information

• Chemical Name: (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate
• CAS No.: 1585232-81-0
• Molecular Formula: C₆₆H₉₉NO₁₂
• Molecular Weight: 1098.51
• Mol file: 1585232-81-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate 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:

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) → (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate (1585232-81-0) + (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate (1585232-78-5)

Guidance literature:

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; acetonitrile; at 0 ℃; for 1h; Solvent; Overall yield = 71 %; Overall yield = 29 mg; Molecular sieve; Inert atmosphere;

DOI:10.3390/molecules181215153

Reference yield:

phenyl 4,6-O,O-anisylidene-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 (1585232-81-0) + (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate (1585232-78-5)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / water / 1.5 h / 50 °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

4: dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate / acetonitrile; dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere

With dmap; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.3390/molecules181215153

Reference yield:

(2S,3R,4E)-1-O-tert-butyldimethylsilyl-2-octadecanamido-4-octadecene-1,3-diol (1215008-40-4) → (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate (1585232-81-0) + (2,3-di-O-p-methoxybenzyl-D-glucopyranosyl)-(1'→1)-(2S,3R,4E)-2-octadecanamido-4-octadecene-1,3-diol-3,6'-phthalate (1585232-78-5)

Guidance literature:

Multi-step reaction with 4 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

4: dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate / acetonitrile; dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere

With pyridine; dmap; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.3390/molecules181215153

upstream 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

(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