(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

Base Information

Chemical Name:(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one
CAS No.:1549989-04-9
Molecular Formula:C₂₅H₄₂O₅Si₂
Molecular Weight:478.776
Hs Code.:

Synonyms:(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

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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 (3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

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Technology Process of (3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

There total 12 articles about (3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one 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: 81.0%

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

: 89466-08-0
2-hydroxyphenyl boronic acid

: 1549989-04-9
(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

Guidance literature:: With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; sodium carbonate; at 65 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetlet.2013.12.052

Reference yield:

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

: 1549989-04-9
(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

Guidance literature:: Multi-step reaction with 4 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

4: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; sodium carbonate / 2 h / 65 °C / Inert atmosphere

With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; mercury(II) diacetate; iodine; sodium carbonate; methanesulfonyl chloride; triethylamine; In pyridine; tetrachloromethane; dichloromethane; water; acetone; 1: |Ferrier Carbohydrate Rearrangement / 4: |Suzuki Coupling;
DOI:10.1016/j.tetlet.2013.12.052

Reference yield:

: 1549988-85-3
C₁₉H₄₀O₅Si₂

: 1549989-04-9
(3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: (bis(tricyclohexyl)phosphine)palladium(II) dichloride; sodium carbonate / 2 h / 65 °C / Inert atmosphere

With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; iodine; sodium carbonate; methanesulfonyl chloride; triethylamine; In pyridine; tetrachloromethane; dichloromethane; 3: |Suzuki Coupling;
DOI:10.1016/j.tetlet.2013.12.052