(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

Base Information

Chemical Name:(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one
CAS No.:1268685-21-7
Molecular Formula:C₂₈H₃₁NO₅
Molecular Weight:461.558
Hs Code.:

Synonyms:(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

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Chemical Property of (3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

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Technology Process of (3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

There total 9 articles about (3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-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: 78.0%

: 1268685-20-6
(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1-hydroxy-2-(trityloxy)ethyl)piperidin-2-one

: 1268685-21-7
(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2010.12.020

Reference yield:

: 1268685-11-5
N-((S)-1-((S)-1,4-dioxaspiro[4.5]decan-2-yl)but-3-enyl)-N-benzylacrylamide

: 1268685-21-7
(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 3 h / 90 °C / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine-N-oxide / water; acetone; tert-butyl alcohol / 24 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

3.2: 1 h / 20 °C

4.1: trifluoroacetic acid / water / 1 h / 0 - 20 °C

5.1: dmap; triethylamine / dichloromethane / 6 h / 20 °C

6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; osmium(VIII) oxide; 4-methylmorpholine-N-oxide; sodium hydride; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2010.12.020

Reference yield:

: 1268685-17-1
(S)-1-benzyl-3,4-dihydroxy-6-((S)-1,4-dioxaspiro[4.5]decan-2-yl)piperidin-2-one

: 1268685-21-7
(3R,4R,6S)-1-benzyl-3,4-bis(benzyloxy)-6-((S)-1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 1 h / 20 °C

2.1: trifluoroacetic acid / water / 1 h / 0 - 20 °C

3.1: dmap; triethylamine / dichloromethane / 6 h / 20 °C

4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With dmap; sodium hydride; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2010.12.020