(1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

Base Information

Chemical Name:(1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane
CAS No.:1499187-53-9
Molecular Formula:C₁₉H₃₀O₄Si
Molecular Weight:350.53
Hs Code.:

Synonyms:

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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 (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

Chemical Property:

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Technology Process of (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

There total 4 articles about (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane 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:

: 1499187-45-9
(1S,4S)-4-(p-acetylphenyl)-1-(t-butyldimethylsiloxy)cyclopent-2-ene

: (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

: 1499187-53-9
(1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

Guidance literature:: With potassium permanganate; In water; acetone; at 50 ℃; for 24h; Overall yield = 90 %; Overall yield = 63 mg; stereoselective reaction; Schlenk technique;
DOI:10.1039/c3cc47551d

Reference yield:

: 68845-72-7
4-tert-butyldimethylsilyloxycyclopentene

: (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

: 1499187-53-9
(1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

Guidance literature:: Multi-step reaction with 2 steps

1: (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane; bis(dibenzylideneacetone)-palladium(0); lithium carbonate / tetrahydrofuran / 15 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique

2: potassium permanganate / acetone; water / 24 h / 50 °C / Schlenk technique

With potassium permanganate; (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane; lithium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; water; acetone; 1: |Heck Reaction;
DOI:10.1039/c3cc47551d

Reference yield:

: 14320-38-8
cyclopent-3-enol

: (1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

: 1499187-53-9
(1S,2S,3S,4R)-4-(p-acetylphenyl)-1-(t-butyldimethylsilyloxy)-2,3-dihydroxycyclopentane

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C / Inert atmosphere; Schlenk technique

2: (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane; bis(dibenzylideneacetone)-palladium(0); lithium carbonate / tetrahydrofuran / 15 h / 80 °C / Inert atmosphere; Glovebox; Schlenk technique

3: potassium permanganate / acetone; water / 24 h / 50 °C / Schlenk technique

With 1H-imidazole; potassium permanganate; (R)-7-bis(m-xylyl)phosphino-7′-bis(3,5-dimethylphenyl)phosphinyl-1,1′-spirobiindane; lithium carbonate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; 2: |Heck Reaction;
DOI:10.1039/c3cc47551d