(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

Base Information

Chemical Name:(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane
CAS No.:155813-64-2
Molecular Formula:C₂₄H₃₄O₃Si
Molecular Weight:398.618
Hs Code.:

Synonyms:(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

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Chemical Property of (2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

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Technology Process of (2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

There total 10 articles about (2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane 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: 74.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 155813-60-8
(3R,4S,5R)-5-((R)-2-Hydroxy-1-methyl-ethyl)-4-methyl-tetrahydro-furan-3-ol

: 155813-64-2
(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 4h;
DOI:10.1021/jo00084a040

Reference yield:

: 74213-65-3
(2R,3R)-3-methyl-butan-1,2,4-triol

: 155813-64-2
(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

Guidance literature:: Multi-step reaction with 9 steps

1: p-toluenesulfonic acid / dimethylformamide / 16 h / Ambient temperature

2: oxalyl chloride, DMSO, (iPr)2EtN / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) r.t., 1.5 h

3: CH₂Cl₂ / 2 h / Ambient temperature

4: 97 percent / 1 N aq. HCl / tetrahydrofuran / 18 h / 25 °C

5: NaHCO₃, I₂ / tetrahydrofuran / 18 h / 25 °C

6: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

7: 78 percent / Bu₃SnH, Et₃B / toluene / 0.5 h / -78 °C

8: 99 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2.5 h

9: 74 percent / N,N-diisopropylethylamine, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / 25 °C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; triethyl borane; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00084a040

Reference yield:

: 74213-61-9
diethyl (2S,3R)-3-hydroxy-2-methylsuccinate

: 155813-64-2
(2R)-1-<(tert-Butyldiphenylsilyl)oxy>-2-<(2R,3R,4R)-4-hydroxy-3-methyltetrahydrofuran-2-yl>propane

Guidance literature:: Multi-step reaction with 10 steps

1: 10 M borane*dimethyl sulfide / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) reflux, 2.5 h

2: p-toluenesulfonic acid / dimethylformamide / 16 h / Ambient temperature

3: oxalyl chloride, DMSO, (iPr)2EtN / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) r.t., 1.5 h

4: CH₂Cl₂ / 2 h / Ambient temperature

5: 97 percent / 1 N aq. HCl / tetrahydrofuran / 18 h / 25 °C

6: NaHCO₃, I₂ / tetrahydrofuran / 18 h / 25 °C

7: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

8: 78 percent / Bu₃SnH, Et₃B / toluene / 0.5 h / -78 °C

9: 99 percent / LiAlH₄ / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 2.5 h

10: 74 percent / N,N-diisopropylethylamine, (N,N-dimethylamino)pyridine / CH₂Cl₂ / 4 h / 25 °C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; triethyl borane; dimethylsulfide borane complex; iodine; tri-n-butyl-tin hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00084a040