(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

Base Information

• Chemical Name: (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one
• CAS No.: 181534-66-7
• Molecular Formula: C₂₉H₄₂O₅Si₂
• Molecular Weight: 526.82
• Mol file: 181534-66-7.mol

Synonyms:(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

Chemical Property of (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one

There total 1 articles about (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-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: 97.0%

1-(Trimethylsilyl)imidazole (18156-74-6) + (R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one (153000-32-9) → (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one (181534-66-7)

Guidance literature:

In dichloromethane; Ambient temperature;

DOI:10.1016/0040-4039(96)01085-4

Reference yield:

(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one (181534-66-7) → (R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-2,5-dihydro-furan-2-ol

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at -78 ℃;

DOI:10.1016/0040-4039(96)01085-4

Reference yield:

(R)-5-[(1R,2R,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-1-trimethylsilanyloxy-propyl]-5H-furan-2-one (181534-66-7) → (2R,3R,3aS,7aR)-3-Benzyloxy-5-methoxy-2-phenyl-hexahydro-furo[3,2-b]pyran-7-one

Guidance literature:

Multi-step reaction with 9 steps

1: DIBALH / diethyl ether / 0.17 h / -78 °C

3: 96 percent / DMAP / CH₂Cl₂ / 1.5 h

4: 89 percent / TBAF-HF / tetrahydrofuran

5: 75 percent / OsO₄, NMO / acetone; H₂O / 1.5 h / Ambient temperature

6: 62 percent / SmI₂ / tetrahydrofuran; ethane-1,2-diol / 10 h / Ambient temperature

7: DIBALH / diethyl ether / 0.17 h / -78 °C

8: 32.6 mg / p-TsOH*H₂O / 15 h / Ambient temperature

9: TPAP, NMO, 4A MS / acetonitrile / 0.5 h / Ambient temperature

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; hydrogen fluoride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethylene glycol; acetone; acetonitrile;

DOI:10.1021/jo970725u

upstream raw materials:

1-(Trimethylsilyl)imidazole

(R)-5-[(1R,2S,3R)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-phenyl-propyl]-5H-furan-2-one

Downstream raw materials:

goniothalenol

(4S,4aS,6R,7R,7aS)-4,7-dihydroxy-6-phenyl-1,5-dioxabicyclo[4.3.0]nonan-2-one

(5S,6R)-6-[(1S,2R)-1-(benzyloxy)-1,2-dihydroxy-2-phenylethyl]-5-hydroxy-5,6-dihydro-2H-pyran-2-one

(1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one