(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester
CAS No.:1054618-19-7
Molecular Formula:C₂₈H₄₃NO₇
Molecular Weight:505.652
Hs Code.:

Synonyms:(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

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Chemical Property of (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

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Technology Process of (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

There total 16 articles about (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl 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: 75.0%

: 35677-83-9,41994-45-0,43041-11-8,90710-04-6
methyl (S)-pipecolinate

: (R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoic acid

: 1054618-19-7
(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

Guidance literature:: With dmap; 2,3,4,5,6-pentafluorophenol; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; dicyclohexyl-carbodiimide;
DOI:10.1016/S0040-4039(00)61612-X

Reference yield:

: 96154-47-1
(R)-2-methyl-1,4-butanediol 4-benzyl ether

: 1054618-19-7
(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: imidazole / dimethylformamide / 0 °C

2: H₂ / 10 percent Pd-C / methanol / Ambient temperature

3: TEA, DCM / 0 °C

4: LiBr, NaHCO₃ / tetrahydrofuran / Ambient temperature

5: 60 percent / 1.) LiNH₂ / liquid ammonia / -33 °C / 1.) 2 h, 2.) 16 h

6: 95 percent / H₂, quinoline / Lindlar's catalyst / methanol

7: (-)-DIPT, TBHP, Ti(O-i-Pr)4, 3 Angstroem molecular sieves, DCM

8: 75 percent / Red-Al / tetrahydrofuran / Ambient temperature

9: Bu₄NF / tetrahydrofuran / Ambient temperature

10: PTSA

11: (COCl)2, DMSO, TEA, DCM / -78 °C

12: 70 percent / Zn / benzene / Heating

13: 70 percent / LiOH / 1,2-dimethoxy-ethane

14: 75 percent / pentafluorophenol, DMAP, dicyclohexylcarbodiimide, DCM

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium hydroxide; lithium amide; oxalyl dichloride; 2,3,4,5,6-pentafluorophenol; 3 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; zinc; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ammonia; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)61612-X

Reference yield:

: 91550-14-0
(2R)-4-(Benzyloxy)-2-methyl-1-butanal

: 1054618-19-7
(S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: NaBH₄ / methanol / 0 °C

2: imidazole / dimethylformamide / 0 °C

3: H₂ / 10 percent Pd-C / methanol / Ambient temperature

4: TEA, DCM / 0 °C

5: LiBr, NaHCO₃ / tetrahydrofuran / Ambient temperature

6: 60 percent / 1.) LiNH₂ / liquid ammonia / -33 °C / 1.) 2 h, 2.) 16 h

7: 95 percent / H₂, quinoline / Lindlar's catalyst / methanol

8: (-)-DIPT, TBHP, Ti(O-i-Pr)4, 3 Angstroem molecular sieves, DCM

9: 75 percent / Red-Al / tetrahydrofuran / Ambient temperature

10: Bu₄NF / tetrahydrofuran / Ambient temperature

11: PTSA

12: (COCl)2, DMSO, TEA, DCM / -78 °C

13: 70 percent / Zn / benzene / Heating

14: 70 percent / LiOH / 1,2-dimethoxy-ethane

15: 75 percent / pentafluorophenol, DMAP, dicyclohexylcarbodiimide, DCM

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium hydroxide; sodium tetrahydroborate; lithium amide; oxalyl dichloride; 2,3,4,5,6-pentafluorophenol; 3 A molecular sieve; TEA; tetrabutyl ammonium fluoride; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium bromide; zinc; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ammonia; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)61612-X