3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester
CAS No.:147806-63-1
Molecular Formula:C₂₂H₃₆O₅Si
Molecular Weight:408.61
Hs Code.:

Synonyms:3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of 3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of 3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

There total 14 articles about 3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester 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: 73.0%

: 2916-68-9
2-(Trimethylsilyl)ethanol

: 147806-62-0
3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester

: 147806-63-1
3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 147806-63-1
3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 70 percent / HOTf / CH₂Cl₂; petroleum ether / 0.5 h / 0 °C

2: 1.) DIBAL / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) benzene, 80 deg C, 0.5 h

3: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

4: 91 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

5: 80 percent / (-)-diethyl tartrate ((-)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 12 h / -20 °C

6: SO₃*py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

7: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / 0 °C

8: 76 percent / TBAF / tetrahydrofuran / 2.5 h / 25 °C

9: 78 percent / CSA / CH₂Cl₂ / 4 h / 25 °C

10: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, 25 deg, 3 h

11: benzene / 2 h / 80 °C

12: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 1.5 h

13: 73 percent / NaH / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; pyridine-SO₃ complex; iso-butyl hydroperoxide; Trifluoromethanesulfonyl fluoride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; ozone; (-)-diethyl tartrate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; Petroleum ether; benzene;

Reference yield:

: 32780-08-8,77697-15-5,112709-13-4,114142-20-0
(5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one

: 147806-63-1
3-((2S,3R,6S)-6-Benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-yl)-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) DIBAL / 1.) CH₂Cl₂, -78 deg C, 0.5 h, 2.) benzene, 80 deg C, 0.5 h

2: 96 percent / imidazole / dimethylformamide / 12 h / 25 °C

3: 91 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

4: 80 percent / (-)-diethyl tartrate ((-)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 12 h / -20 °C

5: SO₃*py, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

6: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / 0 °C

7: 76 percent / TBAF / tetrahydrofuran / 2.5 h / 25 °C

8: 78 percent / CSA / CH₂Cl₂ / 4 h / 25 °C

9: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, 25 deg, 3 h

10: benzene / 2 h / 80 °C

11: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 1.5 h

12: 73 percent / NaH / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; pyridine-SO₃ complex; iso-butyl hydroperoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; ozone; (-)-diethyl tartrate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; benzene;