2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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Chemical Name:2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester
CAS No.:863659-98-7
Molecular Formula:C₂₅H₄₀O₅Si
Molecular Weight:448.675
Hs Code.:

Synonyms:2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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Chemical Property of 2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

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Technology Process of 2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

There total 17 articles about 2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-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: 89.0%

: 677707-79-8
2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

: 863659-98-7
2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: 2-[(2R,6S)-6-((R)-2-Benzyloxy-pent-4-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; at 20 ℃;

With sodium periodate; In water; acetone; at 20 ℃; for 0.5h;
DOI:10.1021/jo0507993

Reference yield:

: 677707-78-7
2-((2R,6S)-6-Methoxycarbonylmethyl-tetrahydro-pyran-2-yl)-2-methyl-propionic acid methyl ester

: 863659-98-7
2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / KOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

2.1: 97 percent / BH₃*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C

3.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

4.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C

4.2: 92 percent / NaOH; H₂O₂ / tetrahydrofuran / 0.17 h / 20 °C

5.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

6.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating

7.1: OsO₄; 4-methylmorpholine N-oxide / H₂O; acetone / 20 °C

7.2: 89 percent / NaIO₄ / H₂O; acetone / 0.5 h / 20 °C

With pyridine; titanium(IV) isopropylate; potassium hydroxide; osmium(VIII) oxide; Trimethyl borate; dimethylsulfide borane complex; sulfur trioxide; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 4.1: Brown allylation;
DOI:10.1021/jo0507993

Reference yield:

: 863659-93-2
(R)-6-Iodo-3-((E)-2-methoxycarbonyl-vinyloxy)-2,2-dimethyl-hexanoic acid methyl ester

: 863659-98-7
2-[(2R,6S)-6-((S)-2-Benzyloxy-4-oxo-butyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / hypophosphorous acid; 1-ethylpiperidine; Et₃B / ethanol / 0.5 h / 20 °C

2.1: 100 percent / KOH / H₂O; methanol; tetrahydrofuran / 3 h / 20 °C

3.1: 97 percent / BH₃*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C

4.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

5.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C

5.2: 92 percent / NaOH; H₂O₂ / tetrahydrofuran / 0.17 h / 20 °C

6.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C

7.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating

8.1: OsO₄; 4-methylmorpholine N-oxide / H₂O; acetone / 20 °C

8.2: 89 percent / NaIO₄ / H₂O; acetone / 0.5 h / 20 °C

With 1-ethyl-piperidine; pyridine; titanium(IV) isopropylate; potassium hydroxide; osmium(VIII) oxide; Trimethyl borate; triethyl borane; dimethylsulfide borane complex; sulfur trioxide; hypophosphorous acid; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; B-chlorodiisopinocampheylborane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 5.1: Brown allylation;
DOI:10.1021/jo0507993