(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

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Chemical Name:(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran
CAS No.:850249-53-5
Molecular Formula:C₄₄H₄₉N₃O₆
Molecular Weight:715.89
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

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Chemical Property of (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

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Technology Process of (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

There total 4 articles about (2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran 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: 94.0%

: 850249-50-2
(2R,3R,4R,5R,6R)-6-(5-Azido-pentyloxymethyl)-4,5-bis-benzyloxy-2-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran-3-ol

: 100-39-0
benzyl bromide

: 850249-53-5
(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 15h;
DOI:10.1021/ol050119i

Reference yield:

: 170219-37-1
3,4-di-O-benzyl-6-O-(5'-azidopentyl)-β-D-glucal

: 850249-53-5
(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMDO / CH₂Cl₂

1.2: 181.9 mg / ZnCl₂ / tetrahydrofuran; diethyl ether / 48 h / -78 - 20 °C

2.1: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 15 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol050119i

Reference yield:

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

: 850249-53-5
(2R,3R,4S,5R,6R)-2-(5-Azido-pentyloxymethyl)-3,4,5-tris-benzyloxy-6-(2-naphthalen-2-yl-ethoxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: 342 mg / NaH / diethyl ether / 4 h / 20 °C

3.1: DMDO / CH₂Cl₂

3.2: 181.9 mg / ZnCl₂ / tetrahydrofuran; diethyl ether / 48 h / -78 - 20 °C

4.1: 94 percent / NaH; Bu₄NI / tetrahydrofuran / 15 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol050119i