(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

Base Information

Chemical Name:(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran
CAS No.:537007-20-8
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

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Chemical Property of (2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

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Technology Process of (2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

There total 1 articles about (2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran 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: 99.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 343949-98-4
(2'S,3'R,5'R)-2-(5'benzyloxymethyl-3'-methyl-tetrahydrofuran-2'-yl)-ethanol

: 537007-20-8
(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(03)00142-X

Reference yield:

: 537007-20-8
(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

: (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-1-((2R,4R,5S)-5-methoxycarbonylmethyl-4-methyl-tetrahydro-furan-2-yl)-3-methyl-2-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 98 percent / H₂ / Pd-C / ethanol / 6 h / 20 °C

2: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

3: 35 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

4: 96 percent / imidazole / dimethylformamide / 3 h / 20 °C

5: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

6: NaIO₄; potassium phosphate buffer / tetrahydrofuran; H₂O / 1 h / 0 °C / pH 6.8

7: 60 percent / tetrahydrofuran / 0.5 h / -78 °C

8: 92 percent / AcOH / H₂O; tetrahydrofuran / 6 h / 20 °C

9: PPTS / acetone / 1 h / 20 °C

10: SO₃-pyridine complex; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

11: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 0 °C

12: 5.3 mg / methanol; hexane / 1 h / 0 °C

13: 80 percent / PPTS / methanol / 5 h / 55 °C

14: 89 percent / DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; 2-methyl-but-2-ene; potassium phosphate buffer; pyridine-SO₃ complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 7: Grignard reaction / 10: Parikh-Doering oxidation;
DOI:10.1016/S0040-4020(03)00142-X

Reference yield:

: 537007-20-8
(2S,3R,5R)-2-[2-(tert-butyldimethylsilyloxy)ethyl]-5-benzyloxymethyl-3-methyltetrahydrofuran

: (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2R)-1-((2R,4R,5S)-5-methoxycarbonylmethyl-4-methyl-tetrahydro-furan-2-yl)-3-methyl-2-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-3-enyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 98 percent / H₂ / Pd-C / ethanol / 6 h / 20 °C

2: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

3: 35 percent / tetrahydrofuran; diethyl ether / 1 h / 0 °C

4: 98 percent / imidazole / dimethylformamide / 3 h / 20 °C

5: 97 percent / OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 16 h / 20 °C

6: 97 percent / NaIO₄; potassium phosphate buffer / tetrahydrofuran; H₂O / 1 h / 0 °C / pH 6.8

7: 51 percent / tetrahydrofuran / 0.5 h / -78 °C

8: 86 percent / AcOH / H₂O; tetrahydrofuran / 6 h / 20 °C

9: 80 percent / PPTS / acetone / 1 h / 20 °C

10: SO₃-pyridine complex; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 20 °C

11: 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 0 °C

12: 4.3 mg / methanol; hexane / 1 h / 0 °C

13: 84 percent / PPTS / methanol / 5 h / 55 °C

14: 81 percent / DMAP; Et₃N / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; 2-methyl-but-2-ene; potassium phosphate buffer; pyridine-SO₃ complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 7: Grignard reaction / 10: Parikh-Doering oxidation;
DOI:10.1016/S0040-4020(03)00142-X