(2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol

Base Information

• Chemical Name: (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol
• CAS No.: 105763-44-8
• Molecular Formula: C₂₅H₂₁N₃O₅S
• Molecular Weight: 475.525
• Mol file: 105763-44-8.mol

Synonyms:(2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol

Chemical Property of (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol

There total 5 articles about (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-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: 92.0%

(2R,3R)-1-(benzoyloxy)-3-phthalimido-5-hexen-2-ol (105763-43-7) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol (105763-44-8)

Guidance literature:

In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo00376a046

Reference yield:

2,2-Dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol (5694-71-3) → (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol (105763-44-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 43 percent / PPh₃, diethyl azodicarboxylate, phthalimide / tetrahydrofuran / 1.) -10 deg C, 3 h, 2.) 22 deg C, 15 h

2: 94 percent / sulfuric acid / methanol / 1.) 22 deg C, 24 h, 2.) reflux, 3 h

3: 70 percent / pyridine / 16 h / 22 °C

4: 92 percent / tetrahydrofuran / 4 h / Heating

With pyridine; phthalimide; sulfuric acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1021/jo00376a046

Reference yield:

benzoyl chloride (98-88-4) → (2R,3S)-1-(benzoyloxy)-3-phthalimido-2-O-(imidazolylthiocarbonyl)-5-hexen-2-ol (105763-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / pyridine / 16 h / 22 °C

2: 92 percent / tetrahydrofuran / 4 h / Heating

With pyridine; In tetrahydrofuran;

DOI:10.1021/jo00376a046

upstream raw materials:

(2R,3R)-1-(benzoyloxy)-3-phthalimido-5-hexen-2-ol

1,1'-Thiocarbonyldiimidazole

2,2-Dimethyl-alpha-2-propenyl-1,3-dioxolane-4-methanol

benzoyl chloride

Downstream raw materials:

(R)-3-amino-1-(benzoyloxy)-5-hexene

(R)-1-(benzoyloxy)-3-phthalimido-5-hexene