benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Base Information

Chemical Name:benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate
CAS No.:622836-85-5
Molecular Formula:C₄₂H₅₇NO₇S₄Si
Molecular Weight:844.267
Hs Code.:

benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Synonyms:benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

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Chemical Property of benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Chemical Property:

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Technology Process of benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

There total 17 articles about benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate 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: 93.0%

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

: 622836-84-4
benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-5-hydroxy-6-[(3S)-3-hydroxy-6-(methoxymethoxy)hexyl]-2-methylpiperidine-1-carboxylate

: 74-88-4
methyl iodide

: 622836-85-5
benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Guidance literature:: carbon disulfide; benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-5-hydroxy-6-[(3S)-3-hydroxy-6-(methoxymethoxy)hexyl]-2-methylpiperidine-1-carboxylate; With 1H-imidazole; sodium hydride; In tetrahydrofuran; Heating;

methyl iodide; In tetrahydrofuran; Heating;
DOI:10.1021/ol030088w

Reference yield:

: (3S,6E)-3-(benzyloxy)-10-(methoxymethoxy)deca-4,6-dien-1-ol

: 622836-85-5
benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 17 steps

1.1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: 94 percent / I₂ / benzene / Irradiation

3.1: 95 percent / dimethylsulfoxide / 50 °C

4.1: NaOH / methanol; H₂O / Heating

5.1: diethyl ether / 0 °C

6.1: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

7.1: NaIO₄ / H₂O; dimethylformamide / 0.25 h / 0 °C

8.1: 97 percent / H₂ / Pd/C / tetrahydrofuran

9.1: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

10.1: 73 percent / imidazole / dimethylformamide / 20 °C

11.1: tetrahydrofuran / 0 °C

12.1: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

13.1: 93 percent / Zn; aq. AcOH / 60 °C

14.1: H₂ / Pd(OH)2 / methanol

15.1: Na₂CO₃

16.1: aq. NaOH / methanol / 20 °C

17.1: NaH; imidazole / tetrahydrofuran / Heating

17.2: 93 percent / tetrahydrofuran / Heating

With 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; hydrogen; iodine; sodium hydride; sodium cyanoborohydride; sodium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol030088w

Reference yield:

: 622836-80-0
(5E,7E)-(S)-4-Benzyloxy-11-methoxymethoxy-undeca-5,7-dienenitrile

: 622836-85-5
benzyl (2S,3S,5S,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-[(3S)-6-(methoxymethoxy)-3-{[(methylsulfanyl)carbothioyl]oxy}hexyl]-2-methyl-5-{[(methylsulfanyl)carbothioyl]oxy}piperidine-1-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaOH / methanol; H₂O / Heating

2.1: diethyl ether / 0 °C

3.1: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

4.1: NaIO₄ / H₂O; dimethylformamide / 0.25 h / 0 °C

5.1: 97 percent / H₂ / Pd/C / tetrahydrofuran

6.1: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

7.1: 73 percent / imidazole / dimethylformamide / 20 °C

8.1: tetrahydrofuran / 0 °C

9.1: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

10.1: 93 percent / Zn; aq. AcOH / 60 °C

11.1: H₂ / Pd(OH)2 / methanol

12.1: Na₂CO₃

13.1: aq. NaOH / methanol / 20 °C

14.1: NaH; imidazole / tetrahydrofuran / Heating

14.2: 93 percent / tetrahydrofuran / Heating

With 1H-imidazole; potassium hydroxide; sodium hydroxide; sodium periodate; (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; hydrogen; sodium hydride; sodium cyanoborohydride; sodium carbonate; acetic acid; lithium hexamethyldisilazane; zinc; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/ol030088w