(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

Base Information

Chemical Name:(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine
CAS No.:951345-92-9
Molecular Formula:C₁₂H₂₂BrNO₆
Molecular Weight:356.214
Hs Code.:

Synonyms:(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

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Technology Process of (1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

There total 8 articles about (1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine 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: 89.0%

: 951345-91-8
N-[(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)cyclohex-2-enyl]-2,2,2-trichloroacetamide

: 951345-92-9
(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.25h;
DOI:10.1021/ol701552r

Reference yield:

: 951327-38-1
(1S,2S,5R,6S)-2-(4-methoxybenzyloxy)-3-bromo-5,6-bis(methoxymethoxy)cyclohex-3-enol

: 951345-92-9
(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 18 °C

1.2: 90 percent / triethylamine / tetrahydrofuran / 16 h / 18 °C

2.1: 95 percent / DDQ; water / CH₂Cl₂ / 16 h / 18 °C

3.1: DBU / CH₂Cl₂ / 2 h / 0 - 18 °C

4.1: K₂CO₃ / 1,2-dichloro-benzene / 0.5 h / 165 °C / microwave irradiation

5.1: 89 percent / DIBAL-H / toluene / 0.25 h / -78 °C

With water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene; toluene; 4.1: Overman rearrangement;
DOI:10.1021/ol701552r

Reference yield:

: C₁₄H₁₃BrO₃

: 951345-92-9
(1R,4R,5S,6R)-2-bromo-4,5,6-tris(methoxymethoxy)-cyclohex-2-enamine

Guidance literature:: Multi-step reaction with 8 steps

1.1: OsO₄; NMO

2.1: 84 percent / DIBAL-H / toluene / 3 h / -50 - -40 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 18 °C

3.2: 90 percent / triethylamine / tetrahydrofuran / 16 h / 18 °C

4.1: 95 percent / DDQ; water / CH₂Cl₂ / 16 h / 18 °C

5.1: DBU / CH₂Cl₂ / 2 h / 0 - 18 °C

6.1: K₂CO₃ / 1,2-dichloro-benzene / 0.5 h / 165 °C / microwave irradiation

7.1: 89 percent / DIBAL-H / toluene / 0.25 h / -78 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1,2-dichloro-benzene; toluene; 7.1: Overman rearrangement;
DOI:10.1021/ol701552r