O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

Base Information

Chemical Name:O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate
CAS No.:303191-07-3
Molecular Formula:C₄₅H₅₇NO₆S₂Si
Molecular Weight:800.168
Hs Code.:

O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

Synonyms:O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

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Chemical Property of O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

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Technology Process of O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

There total 18 articles about O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate 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: 98.0%

: 75-15-0,12122-00-8
carbon disulfide

: 303191-06-2
(3S)-1-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methyl-piperidinyl)-5-(methoxymethoxy)-3-pentanol

: 74-88-4
methyl iodide

: 303191-07-3
O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

Guidance literature:: carbon disulfide; (3S)-1-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methyl-piperidinyl)-5-(methoxymethoxy)-3-pentanol; With 1H-imidazole; sodium hydride; In tetrahydrofuran; for 1h; Heating;

methyl iodide; In tetrahydrofuran; for 0.5h; Further stages.; Heating;
DOI:10.1021/jo001589n

Reference yield:

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

: 303191-07-3
O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

Guidance literature:: Multi-step reaction with 18 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

17.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

18.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

18.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

With 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 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

Reference yield:

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

: 303191-07-3
O-{(1S)-3-((2R,3S,5S,6S)-1-benzoyl-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidinyl)-1-[2-(methoxymethoxy)ethyl]propyl} S-methyldithiocarbonate

Guidance literature:: Multi-step reaction with 17 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

16.1: 90 percent / KOH; K₂CO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

17.1: NaH; imidazole / tetrahydrofuran / 1 h / Heating

17.2: 98 percent / tetrahydrofuran / 0.5 h / Heating

With 1H-imidazole; dmap; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; tetrapropylammonium periodate; hydroxylamine hydrochloride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 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