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

Base Information

• Chemical Name: (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol
• CAS No.: 207591-91-1
• Molecular Formula: C₂₀H₂₁IO₄
• Molecular Weight: 452.289
• Mol file: 207591-91-1.mol

Synonyms:(2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol

Chemical Property of (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol

There total 4 articles about (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-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: 74.0%

(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-hydroxymethyl-tetrahydro-furan-3-ol (207591-90-0) → (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol (207591-91-1)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 1h; Heating;

DOI:10.1271/bbb.62.521

Reference yield:

(2S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furan-3-one (195141-43-6) → (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol (207591-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 78 percent / tetrahydrofuran; diethyl ether / 0.5 h / 5 °C

2: 88 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

3: 74 percent / PPh₃, I₂, imidazole / toluene / 1 h / Heating

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1271/bbb.62.521

Reference yield:

(2S,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol (207591-89-7) → (2R,3S,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-benzyl-2-iodomethyl-tetrahydro-furan-3-ol (207591-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / n-Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

2: 74 percent / PPh₃, I₂, imidazole / toluene / 1 h / Heating

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1271/bbb.62.521

upstream raw materials:

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

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

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

benzylmagnesium chloride

Downstream raw materials:

(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

Acetic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester

Benzoic acid (2S,3R)-2-benzo[1,3]dioxol-5-ylmethyl-3-benzyl-3-hydroxy-pent-4-enyl ester