benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Base Information

• Chemical Name: benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
• CAS No.: 1421868-67-8
• Molecular Formula: C₆₁H₇₈O₁₁
• Molecular Weight: 987.284

Synonyms:benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Chemical Property of benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

There total 10 articles about benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 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: 87.0%

benzyl (2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate (1421868-61-2) + 1-hexadecylcarboxylic acid (57-10-3) → benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate (1421868-67-8)

Guidance literature:

With dmap; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50 ℃; for 48h; Inert atmosphere;

DOI:10.1021/jo302508e

Reference yield:

2-O-(4-methoxybenzyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol (544686-85-3) → benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate (1421868-67-8)

Guidance literature:

Multi-step reaction with 6 steps

1: tetra-(n-butyl)ammonium iodide; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 144 h / 20 °C / Molecular sieve; Inert atmosphere

2: sodium methylate / methanol; dichloromethane

3: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; dichloromethane / 3 h / 20 °C

4: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 20 °C

5: pyridine hydrogenfluoride / tetrahydrofuran / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; dmap; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 48 h / 50 °C / Inert atmosphere

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; sodium methylate; tetra-(n-butyl)ammonium iodide; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo302508e

Reference yield:

1-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-3-O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-sn-glyceride (1421868-58-7) → benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate (1421868-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; dichloromethane / 3 h / 20 °C

2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 20 °C

3: pyridine hydrogenfluoride / tetrahydrofuran / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; dmap; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate / N,N-dimethyl-formamide / 48 h / 50 °C / Inert atmosphere

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo302508e

upstream raw materials:

1,6-di-O-(tert-butyldiphenylsilyl)-2,5-di-O-(4-methoxybenzyl)-D-mannitol

(2R)-3-[(tert-butyldiphenylsilyl)oxy]-2-(4-methoxybenzyloxy)propanal

2-O-(4-methoxybenzyl)-1-O-(tert-butyldiphenylsilyl)-sn-glycerol

1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranoside

Downstream raw materials:

benzyl (1-O-palmityl-2-O-((R)-10-methylstearyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate

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