(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

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Chemical Name:(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol
CAS No.:445306-71-8
Molecular Formula:C₃₀H₄₂O₅Si
Molecular Weight:510.746
Hs Code.:

Synonyms:(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

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Chemical Property of (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

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Technology Process of (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

There total 19 articles about (3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-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:

: 527743-02-8
(S)-2-[(E)-(3S,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-6-triethylsilanyloxy-hex-1-enyl]-4-methyl-3,6-dihydro-2H-pyran

: 445306-71-8
(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃;
DOI:10.1016/S0040-4039(02)00472-0

Reference yield:

: 302554-87-6
(S)-2-allyloxy-4-methyl-1-trityloxy-4-pentene

: 445306-71-8
(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: Cl₂(PCy₃)2Ru=CHPh / tetrahydrofuran / 20 °C

2: 84 percent / HCl gas / CH₂Cl₂ / 0.5 h / -10 °C

3: Et₃N; pyr*SO₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 - 5 °C

4: 81 percent / Et₃N; LiCl / tetrahydrofuran / 15 h / 0 °C

5: 94 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0.17 h / -78 °C

6: iPr₂NEt; TBAI / dimethylformamide / 16 h / 20 °C

7: 4.17 g / TsOH / methanol / 0.5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3: Parikh-Doering oxidation;
DOI:10.1021/jo026743f

Reference yield:

: 206660-79-9
(S)-4-methyl-1-(trityloxy)pent-4-en-2-ol

: 445306-71-8
(3S,4S,5E)-3-(tert-butyldiphenylsilanyloxy)-4-methoxymethoxy-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: t-BuOK / tetrahydrofuran / 1 h / 20 - 45 °C

1.2: 92 percent / tetrahydrofuran / 1.5 h / 20 °C

2.1: Cl₂(PCy₃)2Ru=CHPh / tetrahydrofuran / 20 °C

3.1: 84 percent / HCl gas / CH₂Cl₂ / 0.5 h / -10 °C

4.1: Et₃N; pyr*SO₃ / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 - 5 °C

5.1: 81 percent / Et₃N; LiCl / tetrahydrofuran / 15 h / 0 °C

6.1: 94 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0.17 h / -78 °C

7.1: iPr₂NEt; TBAI / dimethylformamide / 16 h / 20 °C

8.1: 4.17 g / TsOH / methanol / 0.5 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; potassium tert-butylate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Parikh-Doering oxidation;
DOI:10.1021/jo026743f