(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

Base Information

Chemical Name:(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine
CAS No.:177341-40-1
Molecular Formula:C₂₁H₃₁NO₈
Molecular Weight:425.479
Hs Code.:

Synonyms:(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

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Chemical Property of (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

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Technology Process of (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

There total 8 articles about (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine 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: 95.0%

: 107-30-2
chloromethyl methyl ether

: 177341-65-0
(2R,4S,6S)-2-Acetoxymethyl-6-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester

: 177341-40-1
(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 15h;
DOI:10.1021/jo9823036

Reference yield:

: 138-60-3
chelidamic acid

: 177341-40-1
(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

Guidance literature:: Multi-step reaction with 8 steps

1: 2,2-dimethoxypropane, HCl / 1.) reflux, 4 h, 2.) room temperature, overnight

2: 7.347 g / hydrogen / rhodium on alumina / H₂O / 15 h / 775.7 Torr / Ambient temperature

3: 90 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

4: 94 percent / diisopropylethylamine / CH₂Cl₂ / 15 h

5: 93 percent / LiBH₄ / tetrahydrofuran / 5 h

6: 93 percent / pyridine, 4-dimethylaminopyridine / 0.5 h / Heating

7: 76 percent / potassium dihydrogen phosphate, sodium hydroxide / acetonitrile; H₂O / 102 h / Ambient temperature; pH 7.0, Aspergillus niger lipase presence, other biologically active materials: pig liver esterase, wheat germ lipase

8: 92 percent / diisopropylethylamine / CH₂Cl₂ / 15 h

With pyridine; hydrogenchloride; dmap; sodium hydroxide; potassium dihydrogenphosphate; lithium borohydride; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo9519569

Reference yield:

: 4-Oxo-1,4-dihydro-pyridine-2,6-dicarboxylic acid dimethyl ester; hydrochloride

: 177341-40-1
(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine

Guidance literature:: Multi-step reaction with 7 steps

1: 7.347 g / hydrogen / rhodium on alumina / H₂O / 15 h / 775.7 Torr / Ambient temperature

2: 90 percent / NaHCO₃ / CH₂Cl₂; H₂O / 4 h / Ambient temperature

3: 94 percent / diisopropylethylamine / CH₂Cl₂ / 15 h

4: 93 percent / LiBH₄ / tetrahydrofuran / 5 h

5: 93 percent / pyridine, 4-dimethylaminopyridine / 0.5 h / Heating

6: 76 percent / potassium dihydrogen phosphate, sodium hydroxide / acetonitrile; H₂O / 102 h / Ambient temperature; pH 7.0, Aspergillus niger lipase presence, other biologically active materials: pig liver esterase, wheat germ lipase

7: 92 percent / diisopropylethylamine / CH₂Cl₂ / 15 h

With pyridine; dmap; sodium hydroxide; potassium dihydrogenphosphate; lithium borohydride; hydrogen; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; Rh/Al₂O₃; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo9519569