(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

Base Information

Chemical Name:(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol
CAS No.:622836-83-3
Molecular Formula:C₃₇H₅₃NO₅Si
Molecular Weight:619.917
Hs Code.:

Synonyms:(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

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Chemical Property of (3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

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Technology Process of (3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

There total 13 articles about (3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-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: 93.0%

: (2S,4aR,5S,7S,8S)-5-(benzyloxy)-7-{[tert-butyl(diphenyl)silyl]oxy}-2-[3-(methoxymethoxy)propyl]-8-methyloctahydropyrido[1,2-b][1,2]oxazine

: 622836-83-3
(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

Guidance literature:: With acetic acid; zinc; at 60 ℃;
DOI:10.1021/ol030088w

Reference yield:

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

: 622836-83-3
(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 91 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 94 percent / I₂ / benzene / Irradiation

3: 95 percent / dimethylsulfoxide / 50 °C

4: NaOH / methanol; H₂O / Heating

5: diethyl ether / 0 °C

6: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

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

8: 97 percent / H₂ / Pd/C / tetrahydrofuran

9: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

10: 73 percent / imidazole / dimethylformamide / 20 °C

11: tetrahydrofuran / 0 °C

12: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

13: 93 percent / Zn; aq. AcOH / 60 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; (+)-(8,8-dichlorocamphorylsulfonyl)-oxaziridine; hydroxylamine hydrochloride; hydrogen; iodine; sodium cyanoborohydride; acetic acid; triethylamine; lithium hexamethyldisilazane; zinc; 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

: 622836-83-3
(3S)-1-((2R,3S,5S,6S)-3-(benzyloxy)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-methylpiperidin-2-yl)-6-(methoxymethoxy)hexan-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: NaOH / methanol; H₂O / Heating

2: diethyl ether / 0 °C

3: 88 percent / NH₂OH*HCl; KOH / methanol / 0 °C

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

5: 97 percent / H₂ / Pd/C / tetrahydrofuran

6: 99 percent / LiHMDS; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine / tetrahydrofuran / -78 °C

7: 73 percent / imidazole / dimethylformamide / 20 °C

8: tetrahydrofuran / 0 °C

9: NaBH₃CN; AcOH / tetrahydrofuran / 0 °C

10: 93 percent / Zn; aq. AcOH / 60 °C

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