(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Base Information

Chemical Name:(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran
CAS No.:302605-77-2
Molecular Formula:C₂₈H₃₂O₅Si
Molecular Weight:476.645
Hs Code.:

Synonyms:(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

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Chemical Property of (2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

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Technology Process of (2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

There total 28 articles about (2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran 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: 86.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 302605-76-1
(2S,3S,4S)-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

: 302605-77-2
(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1271/bbb.64.1563

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: (3S,4S)-5-Benzo[1,3]dioxol-5-yl-4-hydroxymethyl-tetrahydro-furan-3-ol

: 302605-77-2
(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

: (2R,3S,4S)-3-(tert-butyldiphenylsilyl)oxymethyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1271/bbb.64.2320

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 302605-77-2
(2S,3S,4S)-3-(tert-butyldiphenylsilyloxy)methyl-4-hydroxy-2-(3,4-methylenedioxyphenyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 12 steps

1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.25 h / -75 °C

1.2: 56 percent / tetrahydrofuran; hexane / 1 h / -75 °C

2.1: 84 percent / N-ethyldiisopropylamine / CH₂Cl₂ / 3 h / 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

4.1: 14.7 g / pyridine / 1 h / 20 °C

5.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 3 h / Heating

6.1: 85 percent / NaIO₄ / methanol / 3 h / 20 °C

7.1: 71 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 2 h / Heating

8.1: oxalyl chloride; N,N-dimethylformamide / CH₂Cl₂ / 0.5 h / cooling

9.1: 0.89 g / tri-n-butyl hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / Heating

10.1: 86 percent / diisobutylaluminium hydride / CH₂Cl₂; toluene / 0.5 h / -75 °C

11.1: aq. HCl / ethanol / 0.5 h / Heating

12.1: 0.06 g / imidazole / dimethylformamide / 2 h / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl hydride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.2: aldol condensation;
DOI:10.1271/bbb.64.2320