(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

Base Information

Chemical Name:(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one
CAS No.:676144-77-7
Molecular Formula:C₂₀H₃₃NO₄Si
Molecular Weight:379.572
Hs Code.:

Synonyms:(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

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Chemical Property of (1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

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Technology Process of (1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

There total 6 articles about (1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(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: 79.0%

: 676144-76-6
(4'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)piperidin-2-one

: 676144-77-7
(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: With acetic acid; In water; at 80 ℃; for 7h;
DOI:10.1021/jo0357216

Reference yield:

: 100777-91-1
(2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine

: 676144-77-7
(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: TBSOTf / CH₂Cl₂ / 3 h / -85 °C

2: 3.1 g / NaBH₄ / NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

3: 96 percent / DBU / 12 h / 140 °C

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 79 percent / AcOH / H₂O / 7 h / 80 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; t-butyldimethylsiyl triflate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride; In methanol; dichloromethane; water;
DOI:10.1021/jo0357216

Reference yield:

: 100-46-9
benzylamine

: 676144-77-7
(1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: MgSO₄ / diethyl ether / 0 °C

2: TBSOTf / CH₂Cl₂ / 3 h / -85 °C

3: 3.1 g / NaBH₄ / NiCl₂*6H₂O / methanol / 0.67 h / 0 °C

4: 96 percent / DBU / 12 h / 140 °C

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 79 percent / AcOH / H₂O / 7 h / 80 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; t-butyldimethylsiyl triflate; magnesium sulfate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel dichloride; In methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo0357216