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

Base Information

Chemical Name:(2S,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol
CAS No.:909534-04-9
Molecular Formula:C₃₆H₆₆O₆Si₂
Molecular Weight:651.087
Hs Code.:

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

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

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

There total 16 articles about (2S,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol 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

: 909534-04-9
(2S,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / NaH / dimethylformamide

2: 70 percent / BF₃*THF; nBuLi

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

4: imidazole / CH₂Cl₂

5: NaBH₄

With 1H-imidazole; sodium tetrahydroborate; 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

: 909534-04-9
(2S,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol

Guidance literature:: Multi-step reaction with 6 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

6: NaBH₄

With 1H-imidazole; sodium tetrahydroborate; 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

: 909534-04-9
(2S,5R)-6-Benzyloxy-1-{(2S,5S)-5-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-pentyl]-tetrahydro-furan-2-yl}-6-(R)-oxiranyl-5-triethylsilanyloxy-hexan-2-ol

Guidance literature:: Multi-step reaction with 8 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

8.1: NaBH₄

With 1H-imidazole; sodium tetrahydroborate; 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