(3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol

Base Information

• Chemical Name: (3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol
• CAS No.: 732248-81-6
• Molecular Formula: C₁₆H₁₆O₂Se
• Molecular Weight: 319.262
• DSSTox Substance ID: DTXSID801198703
• Mol file: 732248-81-6.mol

Synonyms:(3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol;DTXSID801198703;732248-81-6

Chemical Property of (3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 320.03155
• Heavy Atom Count: 19
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(C(O1)C2=CC=CC=C2)[Se]C3=CC=CC=C3)O
• Isomeric SMILES: C1[C@H]([C@H]([C@@H](O1)C2=CC=CC=C2)[Se]C3=CC=CC=C3)O

Technology Process of (3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol

There total 3 articles about (3R,4R,5S)-Tetrahydro-5-phenyl-4-(phenylseleno)-3-furanol 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: 49.0%

N-phenylselanylphthalimide (71098-88-9) + (2S,3E)-4-phenylbut-3-ene-1,2-diol (229648-88-8) → (3R,4R,5S)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol (732248-81-6) + (3R,4S,5R)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol (732248-75-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2004.05.009

Reference yield:

benzyltriphenylphosphonium bromide (1449-46-3) → (3R,4R,5S)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol (732248-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 - 20 °C

1.2: tetrahydrofuran / 2 h / 0 °C

2.1: 98 percent / hydrochloric acid / tetrahydrofuran / 0.5 h / cooling

3.1: 49 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 - 20 °C

With hydrogenchloride; n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.05.009

Reference yield:

(4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane (147976-19-0) → (3R,4R,5S)-5-phenyl-4-(phenylseleno)tetrahydrofuran-3-ol (732248-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / hydrochloric acid / tetrahydrofuran / 0.5 h / cooling

2: 49 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 - 20 °C

With hydrogenchloride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.05.009

upstream raw materials:

N-phenylselanylphthalimide

(2S,3E)-4-phenylbut-3-ene-1,2-diol

benzyltriphenylphosphonium bromide

(4S)-2,2-dimethyl-4-[(E)-2-phenylethenyl]-1,3-dioxolane

Downstream raw materials:

(3S,4R,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol

(3S,4S,5R)-4-allyl-5-phenyltetrahydrofuran-3-ol

(3R,4aR,5R,7aS)-5-phenyl-3-(phenylseleno)hexahydro-2H-furo[3,4-b]pyran