(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol
CAS No.:951787-42-1
Molecular Formula:C₂₁H₂₆N₂O₃
Molecular Weight:354.449
Hs Code.:

Synonyms:(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

There total 4 articles about (2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol 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: 75.0%

: 951787-41-0
1,1-dibenzyl-2-((2S,4aR,8S,8aR)-7-methylene-2-phenyl-hexahydropyrano[3,2-d][1,3]dioxin-8-yl)hydrazine

: 951787-42-1
(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 1h;
DOI:10.1016/j.tet.2007.06.117

Reference yield:

: 951787-30-7
1,1-dibenzyl-2-(((2S,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)methylene)hydrazine

: 951787-42-1
(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hydride / various solvent(s); tetrahydrofuran / 0.33 h

1.2: 92 percent / sodium iodide / various solvent(s); tetrahydrofuran / 16 h

2.1: AIBN; tributyltin hydride / dimethylformamide / 16 h / 80 °C

2.2: 80 percent / n-butyl lithium / tetrahydrofuran / 1 h / -78 °C

3.1: 75 percent / p-toluenesulfonic acid / methanol / 1 h

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.06.117

Reference yield:

: 1,1-dibenzyl-2-(((2S,4R,5R)-2-phenyl-5-(prop-2-ynyloxy)-1,3-dioxan-4-yl)methylene)hydrazine

: 951787-42-1
(2R,3R)-4-(2,2-dibenzylhydrazinyl)-2-(hydroxymethyl)-5-methylene-tetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: AIBN; tributyltin hydride / dimethylformamide / 16 h / 80 °C

1.2: 80 percent / n-butyl lithium / tetrahydrofuran / 1 h / -78 °C

2.1: 75 percent / p-toluenesulfonic acid / methanol / 1 h

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2007.06.117