(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

Base Information

Chemical Name:(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester
CAS No.:1647153-68-1
Molecular Formula:C₃₇H₄₃NO₆
Molecular Weight:597.752
Hs Code.:

Synonyms:(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

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Chemical Property of (2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

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Technology Process of (2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

There total 7 articles about (2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester 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: 63.0%

: 111-66-0,25068-25-1
oct-1-ene

: 1647153-67-0
(2S,3S)-O-acryloyl-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

: 1647153-68-1
(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 4h; Inert atmosphere; Reflux;
DOI:10.3762/bjoc.10.113

Reference yield:

: 1647153-64-7
(2R,3S)-3-O-acryloyl-1-O-(tert-butyldimethylsilyl)-2-(fluorenylmethyloxycarbonyl-amino)-4-methyl-pentane-1,3-diol

: 1647153-68-1
(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: acetyl chloride / methanol / 3 h / 0 °C / Inert atmosphere

2: sodium hydrogencarbonate; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid / water; acetone / 4.22 h / 0 °C

3: caesium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; caesium carbonate; acetyl chloride; sodium bromide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.3762/bjoc.10.113

Reference yield:

: 1647153-65-8
(2R,3S)-3-O-acryloyl-2-(fluorenylmethyloxycarbonylamino)-4-methyl-pentane-1,3-diol

: 1647153-68-1
(2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydrogencarbonate; sodium bromide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid / water; acetone / 4.22 h / 0 °C

2: caesium carbonate / N,N-dimethyl-formamide / 17 h / 20 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; trichloroisocyanuric acid; sodium hydrogencarbonate; caesium carbonate; sodium bromide; In dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.3762/bjoc.10.113