(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

Base Information

• Chemical Name: (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one
• CAS No.: 195141-43-6
• Molecular Formula: C₂₉H₃₂O₅Si
• Molecular Weight: 488.656
• Mol file: 195141-43-6.mol

Synonyms:(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

Chemical Property of (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one

There total 4 articles about (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-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: 94.0%

(2S,3R,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol (195141-40-3) → (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one (195141-43-6)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1271/bbb.61.1342

Reference yield:

5-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-benzo[1,3]dioxole (195141-37-8) → (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one (195141-43-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / HCl / tetrahydrofuran; methanol; H₂O / 5 h / Ambient temperature

2: 94 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1271/bbb.61.1342

Reference yield:

(3R,4R,5S)-3-[Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-ol → (2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one (195141-43-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.18 g / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 1 h / 2 °C

2: 86 percent / HCl / tetrahydrofuran; methanol; H₂O / 5 h / Ambient temperature

3: 94 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; triethylsilane; boron trifluoride diethyl etherate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1271/bbb.61.1342

upstream raw materials:

(2S,3R,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

5-[(3S,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ylmethyl]-benzo[1,3]dioxole

Downstream raw materials:

((2R,4R)-4-Benzo[1,3]dioxol-5-ylmethyl-3-methylene-tetrahydro-furan-2-ylmethoxy)-tert-butyl-diphenyl-silane

(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

(2S,3R)-2-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-pent-4-ene-1,3-diol

(3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-tetrahydro-furan-2,3-diol