(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol
CAS No.:755017-97-1
Molecular Formula:C₂₂H₂₅BrN₆O₃
Molecular Weight:501.383
Hs Code.:

Synonyms:(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

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Chemical Property of (1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

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Technology Process of (1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

There total 7 articles about (1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol 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:

: 840524-49-4
(3aS,4R,5S,7R,7aS)-5,7-Diazido-4-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

: 755017-97-1
(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

Guidance literature:: With acetic acid; In 1,4-dioxane; at 75 - 80 ℃; for 10h;
DOI:10.1021/ja048936l

Reference yield:

: 6337-67-3
4,4'-bis(bromomethyl)bibenzyl

: 755017-97-1
(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 40 percent / NaH; TBAI / dimethylformamide / 2 h / 20 °C

2: aq. acetic acid / dioxane / 10 h / 75 - 80 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/ja048936l

Reference yield:

: 236115-61-0
[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

: 755017-97-1
(1S,2R,3R,4S,6R)-4,6-Diazido-3-{4-[2-(4-bromomethyl-phenyl)-ethyl]-benzyloxy}-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 93 percent / sodium methoxide / methanol / 5 h / 20 °C

3: 95 percent / p-toluenesulfonic acid / 10 h / 20 °C

4: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5: 40 percent / NaH; TBAI / dimethylformamide / 2 h / 20 °C

6: aq. acetic acid / dioxane / 10 h / 75 - 80 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja048936l