(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

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Chemical Name:(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran
CAS No.:143144-71-2
Molecular Formula:C₂₆H₄₅BrO₅Si₂
Molecular Weight:573.715
Hs Code.:

Synonyms:(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

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Chemical Property of (2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

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Technology Process of (2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

There total 4 articles about (2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-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: 85.0%

: 107-30-2
chloromethyl methyl ether

: 143144-64-3
4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol

: 143144-71-2
(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/jo00046a049

Reference yield:

: 3958-82-5
2-bromo-1,4-benzoquinone

: 143144-71-2
(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 1a.) t-BuLi / 1a.) THF, pentane, -78 deg C, 1b.) 0 deg C, 2 h, 2.) THF, -78 deg C, 4 h

2: 87 percent / Na₂S₂O₄ / tetrahydrofuran; H₂O / 5 h / Ambient temperature

3: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 0 °C

With sodium dithionite; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo00046a049

Reference yield:

: 101856-98-8,101915-63-3,129830-33-7
(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

: 143144-71-2
(2S,3S,4S)-6-(3-Bromo-4-methoxymethoxy-phenyl)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

1: 1a.) t-BuLi / 1a.) THF, pentane, -78 deg C, 1b.) 0 deg C, 2 h, 2.) THF, -78 deg C, 4 h

2: 87 percent / Na₂S₂O₄ / tetrahydrofuran; H₂O / 5 h / Ambient temperature

3: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 0 °C

With sodium dithionite; tert.-butyl lithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo00046a049