(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

Base Information

Chemical Name:(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde
CAS No.:676144-79-9
Molecular Formula:C₂₆H₄₅NO₄Si₂
Molecular Weight:491.819
Hs Code.:

Synonyms:(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

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Chemical Property of (2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

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Technology Process of (2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

There total 8 articles about (2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde 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: 91.0%

: 676144-78-8
(1'S,5S,6S)-1-benzyl-6-(1,2-bis(triethylsilanyloxy)ethyl)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one

: 676144-79-9
(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -80 - 25 ℃;
DOI:10.1021/jo0357216

Reference yield:

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

: 676144-79-9
(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

Guidance literature:: Multi-step reaction with 7 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

6: 96 percent / pyridine; DMAP / 1 h / 20 °C

7: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -80 - 25 °C

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

Reference yield:

: 100-46-9
benzylamine

: 676144-79-9
(2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde

Guidance literature:: Multi-step reaction with 8 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

7: 96 percent / pyridine; DMAP / 1 h / 20 °C

8: 91 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -80 - 25 °C

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