2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

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Chemical Name:2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol
CAS No.:638188-75-7
Molecular Formula:C₄₅H₆₂O₆Si
Molecular Weight:727.069
Hs Code.:

2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

Synonyms:2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

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Chemical Property of 2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

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Technology Process of 2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

There total 20 articles about 2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-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: 71.0%

: Acetic acid (R)-1-{2-[(1S,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-4-yl}-2-[(4S,5S,6R)-2,2,5-trimethyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-yl]-propyl ester

: 638188-75-7
2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

Guidance literature:: Acetic acid (R)-1-{2-[(1S,3S)-4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-butyl]-6-methoxy-5-methoxymethoxy-7-methyl-benzofuran-4-yl}-2-[(4S,5S,6R)-2,2,5-trimethyl-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-4-yl]-propyl ester; With hydrogenchloride; In methanol; at 20 ℃; for 15h;

With sodium hydroxide; In methanol; water; at 0 ℃; for 1.5h;

With toluene-4-sulfonic acid; In toluene; at 75 ℃; for 1h;
DOI:10.1021/ol035846x

Reference yield:

: 1760-80-1
2-methoxy-3-methylbenzene-1,4-diol

: 638188-75-7
2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.1: N-bromosuccinimide / CHCl₃ / 48 h / 5 °C

3.1: Mg / tetrahydrofuran / 2 h / Heating

4.1: 96 percent / CuI / 0.5 h / -30 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: TfOH; MS 4 Angstroem / ethanol; toluene / 0.17 h / 80 °C

7.1: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C

8.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / tetrahydrofuran / 1 h / -30 °C

8.2: 88 percent / tetrahydrofuran / 2 h / -78 - -25 °C

9.1: pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / 20 °C

10.1: aq. HCl / methanol / 15 h / 20 °C

10.2: NaOH / methanol; H₂O / 1.5 h / 0 °C

10.3: 71 percent / p-toluenesulfonic acid / toluene / 1 h / 75 °C

With pyridine; hydrogenchloride; dmap; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; MS 4 Angstroem; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 5.1: Swern oxidation;
DOI:10.1021/ol035846x

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 638188-75-7
2-((2S,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentan-2-yl)-4-((2R,3R,4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)tetrahydro-2H-pyran-2-yl)-6-methoxy-7-methylbenzofuran-5-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-BuLi / H₂O; tetrahydrofuran

2.1: lithium tri-sec-butylborohydride / 2 h / -90 - -60 °C

2.2: hexamethylphosphoric triamide / 12 h / -78 °C

3.1: i-Bu₂AlH / 2 h / -78 °C

4.1: n-BuLi / 0 °C

5.1: m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

6.1: 96 percent / CuI / 0.5 h / -30 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: TfOH; MS 4 Angstroem / ethanol; toluene / 0.17 h / 80 °C

9.1: 94 percent / NaH / dimethylformamide / 0.5 h / 0 °C

10.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / tetrahydrofuran / 1 h / -30 °C

10.2: 88 percent / tetrahydrofuran / 2 h / -78 - -25 °C

11.1: pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 h / 20 °C

12.1: aq. HCl / methanol / 15 h / 20 °C

12.2: NaOH / methanol; H₂O / 1.5 h / 0 °C

12.3: 71 percent / p-toluenesulfonic acid / toluene / 1 h / 75 °C

With pyridine; hydrogenchloride; dmap; copper(l) iodide; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; trifluorormethanesulfonic acid; MS 4 Angstroem; L-Selectride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Horner-Wadsworth-Emmons olefination / 7.1: Swern oxidation;
DOI:10.1021/ol035846x