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

Base Information

Chemical Name:(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone
CAS No.:1549988-96-6
Molecular Formula:C₁₉H₃₇IO₄Si₂
Molecular Weight:512.576
Hs Code.:

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

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Chemical Property of (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone

Chemical Property:

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

There total 10 articles about (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-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:

: 1549988-60-4
(((2S,3R,4S,5S)-2,5-dimethoxy-6-methylenetetrahydro-2H-pyran-3,4-diyl)bis(oxy))bis(tert-butyldimethylsilane)

: 1549988-96-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: iodine / tetrachloromethane; pyridine / 24 h / 0 - 20 °C / Inert atmosphere

With mercury(II) diacetate; iodine; methanesulfonyl chloride; triethylamine; In pyridine; tetrachloromethane; dichloromethane; water; acetone; 1: |Ferrier Carbohydrate Rearrangement;
DOI:10.1016/j.tetlet.2013.12.052

Reference yield:

: 1549988-85-3
C₁₉H₄₀O₅Si₂

: 1549988-96-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone

Guidance literature:: Multi-step reaction with 2 steps

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

2: iodine / tetrachloromethane; pyridine / 24 h / 0 - 20 °C / Inert atmosphere

With iodine; methanesulfonyl chloride; triethylamine; In pyridine; tetrachloromethane; dichloromethane;
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

: 1549988-96-6
(4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone

Guidance literature:: Multi-step reaction with 5 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

5.1: iodine / tetrachloromethane; pyridine / 24 h / 0 - 20 °C / Inert atmosphere

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