(R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde

Base Information

• Chemical Name: (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde
• CAS No.: 765923-82-8
• Molecular Formula: C₂₂H₂₈O₃Si
• Molecular Weight: 368.548
• Mol file: 765923-82-8.mol

Synonyms:(R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde

Chemical Property of (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde

There total 6 articles about (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde 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: 90.0%

(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran (765923-81-7) → (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde (765923-82-8)

Guidance literature:

(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran; With ozone; In dichloromethane; at -78 ℃; for 1h;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 4h; Further stages.;

DOI:10.1016/j.tet.2004.06.060

Reference yield:

D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde (765923-82-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 55 percent / aq. NaNO₂; H₂SO₄ / 0 °C

2.1: 80 percent / NH₃*Me₂S / tetrahydrofuran / 0 °C

3.1: 85 percent / Et₃N; DMAP / CH₂Cl₂

4.1: LiHMDS / tetrahydrofuran / -78 °C

5.1: aq. H₂O₂ / CH₂Cl₂ / 0 °C

6.1: 80 percent / CuI; Me₂S / tetrahydrofuran / 2 h / -78 °C

7.1: DIBAL / CH₂Cl₂; toluene / 3 h / -78 °C

8.1: 809 mg / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 3 h / -45 °C

9.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

9.2: 90 percent / PPh₃ / CH₂Cl₂ / 4 h / 20 °C

With triethylsilane; dmap; copper(l) iodide; dimethylsulfide; ammonia, dimethyl sulfide; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; ozone; triethylamine; lithium hexamethyldisilazane; sodium nitrite; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2004.06.060

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-carbaldehyde (765923-82-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 85 percent / Et₃N; DMAP / CH₂Cl₂

2.1: LiHMDS / tetrahydrofuran / -78 °C

3.1: aq. H₂O₂ / CH₂Cl₂ / 0 °C

4.1: 80 percent / CuI; Me₂S / tetrahydrofuran / 2 h / -78 °C

5.1: DIBAL / CH₂Cl₂; toluene / 3 h / -78 °C

6.1: 809 mg / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 3 h / -45 °C

7.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

7.2: 90 percent / PPh₃ / CH₂Cl₂ / 4 h / 20 °C

With triethylsilane; dmap; copper(l) iodide; dimethylsulfide; boron trifluoride diethyl etherate; dihydrogen peroxide; diisobutylaluminium hydride; ozone; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2004.06.060

upstream raw materials:

(2R,3S)-(-)-2-(tert-butyldiphenylsilanyloxymethyl)-3-vinyltetrahydrofuran

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

D-Glutamic acid

(R)-(+)-5-(tert-butyldiphenylsilanyloxymethyl)furan-2(5H)-one

Downstream raw materials:

(S)-1-[(R)-2-(tert-butyldiphenylsilanyloxymethyl)tetrahydrofuran-(R)-3-yl]-4-methyl-(S)-2-nitropentan-1-ol