Phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,9c-tetrahydro-

Base Information

• Chemical Name: Phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,9c-tetrahydro-
• CAS No.: 75947-56-7
• Mol file: 75947-56-7.mol

Synonyms:

Chemical Property of Phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,9c-tetrahydro-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,9c-tetrahydro-

There total 13 articles about Phenanthro(3,4-b)oxirene-2,3-diol, 1a,2,3,9c-tetrahydro- 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: 83.0%

(7R,7aS,10aS,11S)-11-Bromo-7-hydroxy-7,7a,10a,11-tetrahydro-phenanthro[2,3-d][1,3]dioxol-9-one → anti-1,2-trans-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrophenanthrene (67694-87-5,67737-62-6,72074-68-1,72074-69-2,75947-56-7,77123-21-8,77123-22-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1021/ja00176a062

Reference yield:

1-bromo-2-naphthyl p-toluenesulfonate (42768-98-9) → anti-1,2-trans-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrophenanthrene (67694-87-5,67737-62-6,72074-68-1,72074-69-2,75947-56-7,77123-21-8,77123-22-9)

Guidance literature:

Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C

2: H₂ / PtO₂ / benzene; ethanol / 4 h / Ambient temperature

3: BF₃*Et₂O, EtSH / CH₂Cl₂ / 6 h / 0 °C

4: 98 percent

5: 75 percent / BBr₃ / -20 °C

6: 83 percent / NaOH / dioxane; H₂O

With sodium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; boron tribromide; ethanethiol; platinum(IV) oxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; benzene;

DOI:10.1021/ja00176a062

Reference yield:

1-bromo-2-naphthyl p-toluenesulfonate (42768-98-9) → syn-1,2-trans-dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrophenanthrene (67694-87-5,67737-62-6,72074-68-1,72074-69-2,75947-56-7,77123-21-8,77123-22-9)

Guidance literature:

Multi-step reaction with 7 steps

1: n-BuLi / tetrahydrofuran / 4 h / -78 - 20 °C

2: H₂ / PtO₂ / benzene; ethanol / 4 h / Ambient temperature

3: BF₃*Et₂O, EtSH / CH₂Cl₂ / 6 h / 0 °C

4: 98 percent

5: 75 percent / BBr₃ / -20 °C

6: Cr(ClO₄)2, ethylenediamine / dimethylformamide / 0.33 h / 0 °C

7: 1.) N-bromoacetamide (NBA), H₂O, 2.) KO-t-Bu / 1.) THF

With n-butyllithium; chromium(II) perchlorate; boron trifluoride diethyl etherate; potassium tert-butylate; water; hydrogen; boron tribromide; ethylenediamine; ethanethiol; N-bromoacetamide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00176a062

upstream raw materials:

1-bromo-2-naphthyl p-toluenesulfonate

C₁₅H₁₀O₄

trans-1,2-dihydroxy-1,2-dihydrophenanthrene