2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

Base Information

Chemical Name:2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid
CAS No.:1392820-88-0
Molecular Formula:C₂₅H₃₄O₅Si
Molecular Weight:442.627
Hs Code.:

Synonyms:2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

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Chemical Property of 2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

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Technology Process of 2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

There total 10 articles about 2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid 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:

: 1392820-86-8
[(2R,4S,6S)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)tetrahydro-2H-pyran-2-yl]acetic acid

: 1392820-88-0
2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

Guidance literature:: With formic acid; water; In tetrahydrofuran; at 0 ℃; for 3h;
DOI:10.1021/jo301122b

Reference yield:

: 1392820-82-4
(4S,6S)-4-((tert-butyldimethylsilyl)oxy)-6-(2-((tertbutyldiphenylsilyl)oxy)ethyl)tetrahydro-2H-pyran-2-one

: 1392820-88-0
2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 4 h / -78 °C / Inert atmosphere

2.1: pyridine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C / Inert atmosphere

4.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

4.2: 4 h

5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3.5 h / 20 °C

6.1: formic acid; water / tetrahydrofuran / 3 h / 0 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; water; diisobutylaluminium hydride; ozone; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/jo301122b

Reference yield:

: C₂₉H₄₆O₄Si₂

: 1392820-88-0
2-((2R,4S,6S)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)acetic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / -78 °C / Inert atmosphere

3.1: ozone / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 4 h

4.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3.5 h / 20 °C

5.1: formic acid; water / tetrahydrofuran / 3 h / 0 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; water; ozone; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo301122b