(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

Base Information

Chemical Name:(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol
CAS No.:1426145-97-2
Molecular Formula:C₃₀H₄₆O₇Si
Molecular Weight:546.777
Hs Code.:

Synonyms:(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

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Chemical Property of (2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

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Technology Process of (2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

There total 16 articles about (2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-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: 97.0%

: 1426145-96-1
(5S,6R)-5-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-9,9-diethyl-6-(methoxymethoxy)-2,4,8-trioxa-9-silaundecane

: 1426145-97-2
(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 0 ℃;
DOI:10.1021/acs.orglett.7b00217

Reference yield:

: 1426145-90-5
(3R,5R)-5-((1R,2R)-3-((tert-butyldiphenylsilyl)oxy)-1,2-dihydroxypropyl)-3-methyldihydrofuran-2(3H)-one

: 1426145-97-2
(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 h / 0 - 60 °C

2: diisobutylaluminium hydride / dichloromethane; hexane; methanol / 1.33 h / -78 °C

3: acetonitrile / 20 h / Reflux

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 - 25 °C

5: 1H-imidazole / dichloromethane / 1 h / 0 °C

6: lithium aluminium tetrahydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

7: 1H-imidazole / dichloromethane / 0.5 h / 0 °C

8: pyridinium p-toluenesulfonate / dichloromethane; methanol / 1 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3: |Wittig Rearrangement;
DOI:10.1021/ol303515h

Reference yield:

: 1426145-91-6
(3R,5R)-5-((5S,6R)-6-(methoxymethoxy)-10,10-dimethyl-9,9-diphenyl-2,4,8-trioxa-9-silaundecan-5-yl)-3-methyldihydrofuran-2(3H)-one

: 1426145-97-2
(2R,3S)-3-((2R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-methyltetrahydrofuran-2-yl)-2,3-bis(methoxymethoxy)propan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / dichloromethane; hexane; methanol / 1.33 h / -78 °C

2: acetonitrile / 20 h / Reflux

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 - 25 °C

4: 1H-imidazole / dichloromethane / 1 h / 0 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

6: 1H-imidazole / dichloromethane / 0.5 h / 0 °C

7: pyridinium p-toluenesulfonate / dichloromethane; methanol / 1 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 2: |Wittig Rearrangement;
DOI:10.1021/ol303515h