(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

Base Information

Chemical Name:(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone
CAS No.:1549988-88-6
Molecular Formula:C₁₉H₃₈O₄Si₂
Molecular Weight:386.679
Hs Code.:

Synonyms:(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

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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 (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

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Technology Process of (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

There total 10 articles about (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone 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: 65.0%

: 1549988-85-3
C₁₉H₄₀O₅Si₂

: 1549988-88-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.tetlet.2013.12.052

Reference yield:

: 1549988-77-3
(2R,3R,4S,5R,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-ol

: 1549988-88-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole; triphenylphosphine / tetrahydrofuran / 60 °C

1.2: 3 h / 60 °C

2.1: tetrahydrofuran / Inert atmosphere

2.2: 2 h / -30 - 20 °C / Inert atmosphere

3.1: mercury(II) diacetate / acetone; water / 0.25 h / 20 °C

4.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 20 °C

With 1H-imidazole; mercury(II) diacetate; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone; 3.1: |Ferrier Carbohydrate Rearrangement;
DOI:10.1016/j.tetlet.2013.12.052

Reference yield:

: 1549988-82-0
(2S,3R,4S,5R,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran-3-ol

: 1549988-88-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / Inert atmosphere

1.2: 2 h / -30 - 20 °C / Inert atmosphere

2.1: mercury(II) diacetate / acetone; water / 0.25 h / 20 °C

3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 20 °C

With mercury(II) diacetate; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; 2.1: |Ferrier Carbohydrate Rearrangement;
DOI:10.1016/j.tetlet.2013.12.052