2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

Base Information

Chemical Name:2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
CAS No.:1333920-16-3
Molecular Formula:C₆₂H₉₉NO₈S
Molecular Weight:1018.54
Hs Code.:

Synonyms:2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

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Chemical Property of 2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

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Technology Process of 2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

There total 14 articles about 2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol 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: 72.0%

: 1333920-15-2
2-hexacosanoylamino-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

: 1333920-16-3
2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

Guidance literature:: With hydrogenchloride; In 1,4-dioxane; methanol; dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.07.103

Reference yield:

: 110-53-2
1-Bromopentane

: 1333920-16-3
2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

Guidance literature:: Multi-step reaction with 13 steps

1.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere

1.2: 60 °C / Inert atmosphere

1.3: Inert atmosphere; Cooling with ice

2.1: pyridine / dichloromethane / 5 h / 20 °C / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol; dichloromethane / 20 °C / Inert atmosphere

6.1: sodium azide / N,N-dimethyl-formamide / 48 h / 50 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / 24 h / 20 °C / Inert atmosphere

8.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

9.1: lithium iodide / N,N-dimethyl-formamide / 24 h / 70 °C / Inert atmosphere

10.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate / water; ethyl acetate / 24 h / 20 °C / pH 8.5 / Inert atmosphere

11.1: trimethylphosphane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

11.2: 2 h / 20 °C / Inert atmosphere

12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 20 °C / Inert atmosphere

13.1: hydrogenchloride / 1,4-dioxane; methanol; dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; methanol; sodium azide; di-isopropyl azodicarboxylate; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium iodide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1.2: Grignard reaction / 3.1: Mitsunobu reaction / 3.2: Mitsunobu reaction / 11.1: Staudinger reaction / 11.2: Staudinger reaction;
DOI:10.1016/j.tetlet.2011.07.103

Reference yield:

: 1333920-07-2
1,3-O-benzylidene-2-O-methanesulfonyl-1-xylo-1,2,3,4-nonanetetrol

: 1333920-16-3
2-hexacosanoylamino-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

Guidance literature:: Multi-step reaction with 11 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol; dichloromethane / 20 °C / Inert atmosphere

4.1: sodium azide / N,N-dimethyl-formamide / 48 h / 50 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / 24 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 20 °C / Inert atmosphere

7.1: lithium iodide / N,N-dimethyl-formamide / 24 h / 70 °C / Inert atmosphere

8.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate / water; ethyl acetate / 24 h / 20 °C / pH 8.5 / Inert atmosphere

9.1: trimethylphosphane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

9.2: 2 h / 20 °C / Inert atmosphere

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 h / 20 °C / Inert atmosphere

11.1: hydrogenchloride / 1,4-dioxane; methanol; dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; methanol; sodium azide; di-isopropyl azodicarboxylate; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium iodide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1.1: Mitsunobu reaction / 1.2: Mitsunobu reaction / 9.1: Staudinger reaction / 9.2: Staudinger reaction;
DOI:10.1016/j.tetlet.2011.07.103