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

Base Information

• Chemical Name: 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol
• CAS No.: 143144-64-3
• Molecular Formula: C₂₄H₄₁BrO₄Si₂
• Molecular Weight: 529.662

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

Chemical Property of 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol

Chemical Property:

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Technology Process of 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol

There total 3 articles about 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol 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: 87.0%

4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-4-hydroxy-cyclohexa-2,5-dienone (143170-95-0) → 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol (143144-64-3)

Guidance literature:

With sodium dithionite; In tetrahydrofuran; water; for 5h; Ambient temperature;

DOI:10.1021/jo00046a049

Reference yield:

2-bromo-1,4-benzoquinone (3958-82-5) → 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol (143144-64-3)

Guidance literature:

Multi-step reaction with 2 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

With sodium dithionite; tert.-butyl lithium; In tetrahydrofuran; water;

DOI:10.1021/jo00046a049

Reference yield:

(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran (101856-98-8,101915-63-3,129830-33-7) → 4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-phenol (143144-64-3)

Guidance literature:

Multi-step reaction with 2 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

With sodium dithionite; tert.-butyl lithium; In tetrahydrofuran; water;

DOI:10.1021/jo00046a049

upstream raw materials:

4-[(4S,5S,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5,6-dihydro-4H-pyran-2-yl]-2-bromo-4-hydroxy-cyclohexa-2,5-dienone

2-bromo-1,4-benzoquinone

(2R,3R,4R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-3,4-dihydro-2H-pyran

Downstream raw materials:

(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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