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

Base Information

• Chemical Name: 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol
• CAS No.: 1333920-11-8
• Molecular Formula: C₃₉H₅₁N₃O₇S
• Molecular Weight: 705.916

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

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

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol

There total 10 articles about 2-azido-3,4-O-isopropylidene-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: 65.0%

2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose (1042397-88-5) + 2-azido-1-iodo-3,4-O-isopropylidene-D-ribo-3,4-nonanediol (1333920-10-7) → 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol (1333920-11-8)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In water; ethyl acetate; at 20 ℃; for 24h; pH=8.5; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.07.103

Reference yield:

1,3-O-benzylidene-1-xylo-1,2,3,4-nonanetetrol (1333920-06-1) → 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol (1333920-11-8)

Guidance literature:

Multi-step reaction with 9 steps

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

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

2.2: 20 °C / Inert atmosphere

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

3.2: 20 °C / Inert atmosphere

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

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

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

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

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

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

With pyridine; methanol; sodium azide; di-isopropyl azodicarboxylate; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction / 2.2: Mitsunobu reaction;

DOI:10.1016/j.tetlet.2011.07.103

Reference yield:

1,3-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol (1333920-08-3) → 2-azido-3,4-O-isopropylidene-1-((2,3,4-tri-O-benzyl-α-D-galactopyranosyl)thio)-D-ribo-3,4-nonanediol (1333920-11-8)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 20 °C / Inert atmosphere

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

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

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

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

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

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

With pyridine; methanol; sodium azide; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium iodide; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.07.103

upstream raw materials:

2,3,4-tri-O-benzyl-1-thio-α-D-galactopyranose

2-azido-1-iodo-3,4-O-isopropylidene-D-ribo-3,4-nonanediol

1,3-O-benzylidene-2-O-methanesulfonyl-1-xylo-1,2,3,4-nonanetetrol

1,3-O-benzylidene-2-O-methanesulfonyl-4-O-p-nitrobenzoyl-D-arabino-1,2,3,4-nonanetetrol

Downstream raw materials:

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

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

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

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

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