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

Base Information

Chemical Name:(2S,3S,4R)-2-hydroxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside
CAS No.:1215176-65-0
Molecular Formula:C₅₀H₆₈O₁₁
Molecular Weight:845.083
Hs Code.:

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

There total 20 articles about (2S,3S,4R)-2-hydroxy-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: 61.0%

: 1215176-64-9
(2S,3S,4R)-3,4-O-isopropylidene-11-octadecyn-1,2-diol

: 676485-51-1
trichloroacetimidoyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-α-D-galactopyranoside

: 1242143-99-2
(2S,3S,4R)-2-hydroxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-β-D-galactopyranoside

: 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

Guidance literature:: With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 5h; Molecular sieve;
DOI:10.1016/j.carres.2010.05.003

Reference yield:

: 37011-88-4
tridec-6-yn-1-ol

: 1242143-99-2
(2S,3S,4R)-2-hydroxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-β-D-galactopyranoside

: 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

Guidance literature:: Multi-step reaction with 12 steps

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

2.1: sodium iodide / acetone / 16 h / Reflux

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

3.2: 0.5 h / -40 - -30 °C / Inert atmosphere

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

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

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

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

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 1 h / 20 °C

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

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

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

12.1: dichloromethane / 0.5 h / Molecular sieves 4?

12.2: 5 h / 0 - 20 °C

With methanol; dmap; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sodium methylate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; pentane;

Reference yield:

: 1215176-38-7
1-iodo-6-tridecyne

: 1242143-99-2
(2S,3S,4R)-2-hydroxy-3,4-O-isopropylidene-11-octadecynyl 4,6-O-benzylidene-2,3-di-O-(4-methoxybenzyl)-β-D-galactopyranoside

: 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

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 0.5 h / -40 - -30 °C / Inert atmosphere

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

With methanol; dmap; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; sodium methylate; toluene-4-sulfonic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane;