(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

Base Information

Chemical Name:(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one
CAS No.:909534-03-8
Molecular Formula:C₃₆H₆₄O₆Si₂
Molecular Weight:649.072
Hs Code.:

(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

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Chemical Property of (R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

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Technology Process of (R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

There total 15 articles about (R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one 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:

: 909534-00-5
Acetic acid (1S,3S)-3-acetoxy-4-bromo-1-bromomethyl-2-hydroxy-butyl ester

: 909534-03-8
(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / NaH / dimethylformamide

2: 70 percent / BF₃*THF; nBuLi

3: PdCl₂(CH₃CN)2 / CH₂Cl₂; H₂O / 20 °C

4: imidazole / CH₂Cl₂

With 1H-imidazole; n-butyllithium; boron trifluoride-tetrahydrofuran complex; sodium hydride; dichloro bis(acetonitrile) palladium(II); In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.06.060

Reference yield:

: 909533-98-8
Bis-((R)-2-ethoxy-2-methyl-[1,3]dioxolan-4-yl)-methanol

: 909534-03-8
(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: CH₂Cl₂

2: 50 percent / NaH / dimethylformamide

3: 70 percent / BF₃*THF; nBuLi

4: PdCl₂(CH₃CN)2 / CH₂Cl₂; H₂O / 20 °C

5: imidazole / CH₂Cl₂

With 1H-imidazole; n-butyllithium; boron trifluoride-tetrahydrofuran complex; sodium hydride; dichloro bis(acetonitrile) palladium(II); In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.06.060

Reference yield:

: 433268-15-6
(S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-ol

: 909534-03-8
(R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Et₃N

2.1: TiCl₄; iPr₂NEt / CH₂Cl₂ / -40 °C

3.1: 75 percent / DIBAL / -78 °C

4.1: PPh₃

4.2: 70 percent / nBuLi

5.1: 70 percent / BF₃*THF; nBuLi

6.1: PdCl₂(CH₃CN)2 / CH₂Cl₂; H₂O / 20 °C

7.1: imidazole / CH₂Cl₂

With 1H-imidazole; n-butyllithium; boron trifluoride-tetrahydrofuran complex; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dichloro bis(acetonitrile) palladium(II); In dichloromethane; water; 4.1: Corey-Fuchs-MacKelvie raction;
DOI:10.1016/j.tetlet.2006.06.060