(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

Base Information

Chemical Name:(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside
CAS No.:1215176-66-1
Molecular Formula:C₇₆H₁₁₈O₁₂
Molecular Weight:1223.77
Hs Code.:

Synonyms:(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

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Chemical Property of (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

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Technology Process of (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

There total 22 articles about (2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside 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: 31.0%

: 506-46-7
1-hexacosanoic acid

: 1215176-65-0
(2S,3S,4R)-2-hydroxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

: 1215176-66-1
(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; at 20 ℃; for 120h;
DOI:10.1016/j.carres.2010.05.003

Reference yield:

: 164576-09-4
4,5-anhydro-1,3-O-benzylidene-D-arabinitol

: 1215176-66-1
(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Cooling with ice

2.1: diethyl ether; pentane; tetrahydrofuran / 16 h / -20 - 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

4.1: dmap / dichloromethane / 3 h / 20 °C

5.1: toluene-4-sulfonic acid / 1 h / 20 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 1 h / 20 °C

7.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / -20 - 20 °C

8.1: sodium methylate; methanol / methanol / 16 h / 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

10.1: dichloromethane / 0.5 h / Molecular sieves 4?

10.2: 5 h / 0 - 20 °C

11.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; tetrahydrofuran / 120 h / 20 °C

With methanol; dmap; tetrabutyl ammonium fluoride; water; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; pentane;

Reference yield:

: 629-05-0
n-octyne

: 1215176-66-1
(2S,3R,4R)-2-hexacosanoyloxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 15 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / hexane; tetrahydrofuran / -40 °C

1.2: -40 - 20 °C

2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C

3.1: triethylamine / dichloromethane / 0.5 h / 0 °C

4.1: sodium iodide / acetone / 16 h / Reflux

5.1: tert.-butyl lithium / diethyl ether; pentane / 1.08 h / -78 - 20 °C

5.2: 0.5 h / -40 - -30 °C / Inert atmosphere

6.1: diethyl ether; pentane; tetrahydrofuran / 16 h / -20 - 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

8.1: dmap / dichloromethane / 3 h / 20 °C

9.1: toluene-4-sulfonic acid / 1 h / 20 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 1 h / 20 °C

11.1: triphenylphosphine; diethylazodicarboxylate / toluene; tetrahydrofuran / -20 - 20 °C

12.1: sodium methylate; methanol / methanol / 16 h / 20 °C

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 20 °C

14.1: dichloromethane / 0.5 h / Molecular sieves 4?

14.2: 5 h / 0 - 20 °C

15.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; tetrahydrofuran / 120 h / 20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sodium methylate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; pentane;