2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

Base Information

Chemical Name:2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine
CAS No.:543697-43-4
Molecular Formula:C₃₂H₄₀N₄O₆
Molecular Weight:576.693
Hs Code.:

Synonyms:2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

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Chemical Property of 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

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Technology Process of 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

There total 4 articles about 2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine 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: 77.0%

: 6959-47-3
2-chloromethylpyridine hydrochloride

: 543697-42-3
(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ol

: 543697-43-4
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

Guidance literature:: (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.416667h;

2-chloromethylpyridine hydrochloride; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;
DOI:10.1021/jm0205088

Reference yield:

: 170220-11-8
5-azido-1-pentanol

: 543697-43-4
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-di-t-butyl-4-methyl-pyridine / CH₂Cl₂ / 0.25 h / 0 °C

2.1: NaH / 0.25 h / 0 °C

2.2: 88 percent / tetrahydrofuran / 1.5 h / 0 °C

3.1: 80 percent / aq. 2,3-dicyano-5,6-dichloro-1,4-quinone / CH₂Cl₂ / 1.25 h / 0 - 20 °C

4.1: NaH / dimethylformamide / 0.42 h / 0 °C

4.2: 77 percent / tetrabutylammonium iodide / dimethylformamide / 1.5 h / 0 °C

With 2,6-di-tert-butyl-4-methylpyridine; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0205088

Reference yield:

: 170220-06-1
5-azidopentyl trifluoromethanesulfonate

: 543697-43-4
2-[(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxymethyl]-pyridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / 0.25 h / 0 °C

1.2: 88 percent / tetrahydrofuran / 1.5 h / 0 °C

2.1: 80 percent / aq. 2,3-dicyano-5,6-dichloro-1,4-quinone / CH₂Cl₂ / 1.25 h / 0 - 20 °C

3.1: NaH / dimethylformamide / 0.42 h / 0 °C

3.2: 77 percent / tetrabutylammonium iodide / dimethylformamide / 1.5 h / 0 °C

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm0205088