(E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone

Base Information

• Chemical Name: (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone
• CAS No.: 150368-99-3
• Molecular Formula: C₂₉H₄₀O₅Si
• Molecular Weight: 496.719
• Mol file: 150368-99-3.mol

Synonyms:(E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone

Chemical Property of (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone

There total 10 articles about (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone 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:

4-methoxy-benzaldehyde (123-11-5) → (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone (150368-99-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 3 Angstroem sieves / methanol / 40 h / 20 °C

2: imidazole

4: Bu₃SnH

5: Bu₄NF / tetrahydrofuran

6: 1.) NaH

7: DIBAlH

8: 93 percent / Swern oxidation

9: 1.) NaH / 1.) THF

With 1H-imidazole; 3 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)73673-2

Reference yield:

(4aS,6R,7R,7aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-furo[3,2-d][1,3]dioxin-7-ol → (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone (150368-99-3)

Guidance literature:

Multi-step reaction with 8 steps

1: imidazole

3: Bu₃SnH

4: Bu₄NF / tetrahydrofuran

5: 1.) NaH

6: DIBAlH

7: 93 percent / Swern oxidation

8: 1.) NaH / 1.) THF

With 1H-imidazole; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73673-2

Reference yield:

tert-Butyl-[(4aS,6S,7aS)-2-(4-methoxy-phenyl)-tetrahydro-furo[3,2-d][1,3]dioxin-6-ylmethoxy]-dimethyl-silane → (E)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-propenone (150368-99-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Bu₄NF / tetrahydrofuran

2: 1.) NaH

3: DIBAlH

4: 93 percent / Swern oxidation

5: 1.) NaH / 1.) THF

With tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)73673-2

upstream raw materials:

dimethyl <2-(tert-butyldimethylsilyl)-2-oxoethyl>-phosphonate

(2R,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

benzyl bromide

4-methoxy-benzaldehyde

Downstream raw materials:

(S)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(tert-butyl-dimethyl-silanyl)-butan-1-one

(S)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-butyric acid

(S)-3-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-thiobutyric acid S-phenyl ester

(S)-4-[(2S,3S,5S)-5-Benzyloxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-1-(triphenyl-λ⁵-phosphanylidene)-pentan-2-one