(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

Base Information

Chemical Name:(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol
CAS No.:1374646-34-0
Molecular Formula:C₁₉H₃₁NO₆Si
Molecular Weight:397.544
Hs Code.:

Synonyms:(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

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Chemical Property of (2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

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Technology Process of (2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

There total 8 articles about (2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-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: 81.0%

: 1374646-33-9
(3R,4S)-5-((tert-butyldimethylsilyl)oxy)-4-methoxypent-1-en-3-ol

: 58621-55-9
1-allyloxy-3-nitro-benzene

: 1374646-34-0
(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; phenol; In toluene; at 20 ℃; for 1h;
DOI:10.1002/anie.201107874

Reference yield:

: 1267551-60-9
(Z)-tert-butyldimethyl((4-(3-nitrophenoxy)but-2-en-1-yl)oxy)silane

: 1374646-34-0
(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: methanol; (S,S)-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)]; sodium t-butanolate / diethyl ether / 14 h / -55 °C

2: dihydrogen peroxide; sodium hydroxide / diethyl ether; water; ethyl acetate / 0.5 h / -55 - 0 °C

3: Hoveyda-Grubbs catalyst second generation / toluene / 1 h / 20 °C

4: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 3 h / 20 °C / Molecular sieve

5: methanol; (S,S)-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)]; sodium t-butanolate / diethyl ether / 18 h / -55 °C

6: dihydrogen peroxide; sodium hydroxide / diethyl ether; water; ethyl acetate / 0.5 h / -55 - 0 °C

7: Hoveyda-Grubbs catalyst second generation; phenol / toluene / 1 h / 20 °C

With methanol; Hoveyda-Grubbs catalyst second generation; (S,S)-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)]; dihydrogen peroxide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydroxide; sodium t-butanolate; phenol; In diethyl ether; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1002/anie.201107874

Reference yield:

: 1374646-32-8
(R,E)-tert-butyl((2-methoxy-5-(3-nitrophenoxy)pent-3-en-1-yl)oxy)dimethylsilane

: 1374646-34-0
(2S,3R,E)-1-((tert-butyldimethylsilyl)oxy)-2-methoxy-6-(3-nitrophenoxy)hex-4-en-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: methanol; (S,S)-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)]; sodium t-butanolate / diethyl ether / 18 h / -55 °C

2: dihydrogen peroxide; sodium hydroxide / diethyl ether; water; ethyl acetate / 0.5 h / -55 - 0 °C

3: Hoveyda-Grubbs catalyst second generation; phenol / toluene / 1 h / 20 °C

With methanol; Hoveyda-Grubbs catalyst second generation; (S,S)-[CuCl(C₁₀H₆N₃(phenyl)2C₆H₂(CH₃)2C(CH₃)3)]; dihydrogen peroxide; sodium hydroxide; sodium t-butanolate; phenol; In diethyl ether; water; ethyl acetate; toluene;
DOI:10.1002/anie.201107874