pereniporin B

Base Information

• Chemical Name: pereniporin B
• CAS No.: 16772-63-7
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 16772-63-7.mol

Synonyms:Naphtho[1,2-c]furan-3(1H)-one,5,5a,6,7,8,9,9a,9b-octahydro-5,9b-dihydroxy-6,6,9a-trimethyl-, [5R-(5a,5ab,9aa,9bb)]-;Naphtho[1,2-c]furan-3(1H)-one, 5,5aa,6,7,8,9,9a,9b-octahydro-5b,9ba-dihydroxy-6,6,9ab-trimethyl-, (-)- (8CI);(-)-Pereniporin B; Pereniporin B

Chemical Property of pereniporin B

Chemical Property:

• Vapor Pressure: 1.61E-10mmHg at 25°C
• Boiling Point: 463°C at 760 mmHg
• Flash Point: 173.4°C
• PSA: 66.76000
• Density: 1.24g/cm³
• LogP: 1.40780

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of pereniporin B

There total 33 articles about pereniporin B 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: 70.0%

methyl (4S,4'S,4a'S,8a'S)-4'a,5',6',7',8',8'a-hexahydro-4'-hydroxy-5',5',8'a-trimethyl-2-oxospiro<1,3-dioxolane-4,1'(4'H)-naphthalene>-2'-carboxylate (121617-64-9) → (-)-pereniporin B (16772-63-7)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 1h; Ambient temperature;

Reference yield:

(3aR,5aS,9aR,9bS)-6,6,9a-Trimethyl-1,3,3a,4,5,5a,6,7,9a,9b-decahydro-naphtho[1,2-c]furan-5-ol (137266-34-3,137331-26-1) → (-)-pereniporin B (16772-63-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C 2) -78 to 25 deg C

2: 100 percent / H₂ / 10percent Pd-C / ethyl acetate

3: 1) 3N>Br₃ 2) DBU / 1) THF, 25 deg C 2) PhH, reflux

4: 66 percent / (PhSeO)2O / chlorobenzene / 0.08 h / 125 - 130 °C

5: Dibal-H / toluene / -78 °C

6: Ag₂CO₃, Celite / benzene / Heating

With oxalyl dichloride; (PhSeO)2O; Celite; hydrogen; phenyltrimethylammonium tribromide; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver carbonate; palladium on activated charcoal; In ethyl acetate; chlorobenzene; toluene; benzene;

DOI:10.1016/S0040-4039(00)92273-1

Reference yield:

(3aR,5aS,9aR,9bS)-6,6,9a-Trimethyl-1,3a,4,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-c]furan-5-one (137266-35-4) → (-)-pereniporin B (16772-63-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / 10percent Pd-C / ethyl acetate

2: 1) 3N>Br₃ 2) DBU / 1) THF, 25 deg C 2) PhH, reflux

3: 66 percent / (PhSeO)2O / chlorobenzene / 0.08 h / 125 - 130 °C

4: Dibal-H / toluene / -78 °C

5: Ag₂CO₃, Celite / benzene / Heating

With (PhSeO)2O; Celite; hydrogen; phenyltrimethylammonium tribromide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; palladium on activated charcoal; In ethyl acetate; chlorobenzene; toluene; benzene;

DOI:10.1016/S0040-4039(00)92273-1

upstream raw materials:

cinnamodial

(5aS,9aS,9bS)-6,6,9a-Trimethyl-3,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-3,5,9b-triol

methyl (4S,4'S,4a'S,8a'S)-4'a,5',6',7',8',8'a-hexahydro-4'-hydroxy-5',5',8'a-trimethyl-2-oxospiro<1,3-dioxolane-4,1'(4'H)-naphthalene>-2'-carboxylate

C₁₆H₂₂O₄

Downstream raw materials:

(+/-)-cinnamosmolide