(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

Base Information

Chemical Name:(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol
CAS No.:345896-85-7
Molecular Formula:C₃₆H₅₁NO₅Si
Molecular Weight:605.89
Hs Code.:

Synonyms:(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

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Chemical Property of (S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

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Technology Process of (S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

There total 16 articles about (S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol 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:

: 303191-05-1
(2S,4aR,5S,7S,8R)-5-(benzyloxy)-7-{[tert-butyl(diphenyl)silyl]oxy}-2-[2-(methoxymethoxy)ethyl]-8-methyloctahydropyrido[1,2-b][1,2]oxazin

: 345896-85-7
(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

Guidance literature:: With acetic acid; zinc; In water; at 60 ℃; for 1h; 7;
DOI:10.1021/jo001589n

Reference yield:

: 164471-44-7
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol

: 345896-85-7
(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

2.1: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

3.1: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

4.1: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

5.1: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

6.1: 91 percent / dimethylsulfoxide / 1 h / 50 °C

7.1: NaOH / H₂O / 4 h / Heating

8.1: 86 percent / diethyl ether / 0.5 h / 0 °C

9.1: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

10.1: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

11.1: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

12.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

12.2: 1.18 g / (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / 5 h / -78 °C

13.1: imidazole / dimethylformamide / 42 h / 20 °C

14.1: tetrahydrofuran / 0.17 h / 0 °C

14.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

15.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

With 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 10.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo001589n

Reference yield:

: 164577-87-1
ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate

: 345896-85-7
(S)-1-[(2R,3S,5S,6S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-6-methyl-piperidin-2-yl]-5-methoxymethoxy-pentan-3-ol

Guidance literature:: Multi-step reaction with 16 steps

1.1: 97 percent / DIBAL-H / tetrahydrofuran; hexane / 0.5 h / 20 °C

2.1: 85 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

3.1: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C

4.1: 98 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / Heating

5.1: 99 percent / DIBAL-H / CH₂Cl₂; hexane / 4 h / 0 °C

6.1: 90 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 3 h / 0 °C

7.1: 91 percent / dimethylsulfoxide / 1 h / 50 °C

8.1: NaOH / H₂O / 4 h / Heating

9.1: 86 percent / diethyl ether / 0.5 h / 0 °C

10.1: 80 percent / hydroxylamine hydrochloride; KOH / methanol / 1 h / 0 °C

11.1: solid tetrapropylammonium (meta)periodate / H₂O; dimethylformamide / 0.5 h / 0 °C

12.1: 99 percent / H₂ / Pd/C / tetrahydrofuran / 0.5 h

13.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

13.2: 1.18 g / (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / 5 h / -78 °C

14.1: imidazole / dimethylformamide / 42 h / 20 °C

15.1: tetrahydrofuran / 0.17 h / 0 °C

15.2: 82 percent / NaBH₃CN; AcOH / tetrahydrofuran / 1 h / 0 °C

16.1: Zn; AcOH / H₂O / 1 h / 60 °C / 7

With 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 11.1: intramolecular Diels-Alder reaction;
DOI:10.1021/jo001589n