2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

Base Information

Chemical Name:2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester
CAS No.:864514-27-2
Molecular Formula:C₄₅H₆₁NO₁₀Si
Molecular Weight:804.066
Hs Code.:

2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

Synonyms:2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

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Chemical Property of 2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

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Technology Process of 2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

There total 30 articles about 2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl 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: 88.0%

: 864514-18-1
(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(2-oxo-butyl)-tetrahydro-pyran-2-carbonitrile

: 864514-17-0
4,6-bis-(4-methoxy-benzyloxy)-3-methyl-2-(2-oxo-ethyl)-benzoic acid methyl ester

: 864514-27-2
2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

Guidance literature:: (2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(2-oxo-butyl)-tetrahydro-pyran-2-carbonitrile; With phenylborondichloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 2.33333h;

4,6-bis-(4-methoxy-benzyloxy)-3-methyl-2-(2-oxo-ethyl)-benzoic acid methyl ester; In dichloromethane; at -78 ℃; for 3.5h;

With methanol; In dichloromethane; water; at -78 - 0 ℃; for 1.5h; pH=7 - 8;

Reference yield:

: 2,4-dimethoxy-5-methyl-benzoyl chloride

: 864514-27-2
2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 4.82 g / benzene / 0 - 20 °C

2.1: sec-BuLi; CuBr*Me₂S / tetrahydrofuran; cyclohexane / -78 - -15 °C

2.2: 76 percent / tetrahydrofuran; cyclohexane / 1 h / -78 °C

3.1: 81 percent / BBr₃ / CH₂Cl₂ / 5.5 h / -78 - 25 °C

4.1: 73 percent / CH₂Cl₂ / 20 h / 20 °C

5.1: 92 percent / K₂CO₃; Bu₄NI / dimethylformamide / 20 h / 80 °C

6.1: 4-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C

7.1: 408 mg / aq. NaIO₄ / methanol / 1 h / 20 °C

8.1: PhBCl₂; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

8.2: CH₂Cl₂ / 3.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; phenylborondichloride; sec.-butyllithium; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja0537068

Reference yield:

: 864514-37-4
N,N-diethyl-2,4-dimethoxy-5-methyl-benzamide

: 864514-27-2
2-{(2R,3S)-5-[(2R,4R,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-cyano-3,3-dimethyl-tetrahydro-pyran-2-yl]-2-hydroxy-3-methyl-4-oxo-pentyl}-4,6-bis-(4-methoxy-benzyloxy)-3-methyl-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: sec-BuLi; CuBr*Me₂S / tetrahydrofuran; cyclohexane / -78 - -15 °C

1.2: 76 percent / tetrahydrofuran; cyclohexane / 1 h / -78 °C

2.1: 81 percent / BBr₃ / CH₂Cl₂ / 5.5 h / -78 - 25 °C

3.1: 73 percent / CH₂Cl₂ / 20 h / 20 °C

4.1: 92 percent / K₂CO₃; Bu₄NI / dimethylformamide / 20 h / 80 °C

5.1: 4-methylmorpholine-N-oxide; aq. OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C

6.1: 408 mg / aq. NaIO₄ / methanol / 1 h / 20 °C

7.1: PhBCl₂; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

7.2: CH₂Cl₂ / 3.5 h / -78 °C

With sodium periodate; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; phenylborondichloride; sec.-butyllithium; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja0537068