(1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane

Base Information

• Chemical Name: (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane
• CAS No.: 862647-18-5
• Molecular Formula: C₁₈H₁₈O₂
• Molecular Weight: 266.34
• Mol file: 862647-18-5.mol

Synonyms:(1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane

Chemical Property of (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane

There total 15 articles about (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane 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: 89.0%

(2S,4R,5R)-2-benzhydryl-5-bromotetrahydro-2H-pyran-4-ol (1332886-85-7) → (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane (862647-18-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.05.012

Reference yield: 50.3%

(2S)-2-benzhydryl-3,6-dihydro-2H-pyran (862647-16-3) → (1R,4S,6S)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane (862647-19-6) + (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane (862647-18-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1021/jm049021k

Reference yield:

N,N-dimethyl-3,3-diphenylpropan-1-amine (4646-55-3) → (1S,4S,6R)-4-benzhydryl-3,7-dioxabicyclo[4.1.0]heptane (862647-18-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: dihydrogen peroxide / water / 20 °C / Inert atmosphere

2.1: 80 - 180 °C / Neat (no solvent); Pyrolysis under reduced pressure

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

4.1: (R,R)-Jacobsen catalyst; water / 72 h / 20 °C / Cooling with ice; Inert atmosphere

5.1: copper(l) iodide / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

5.2: 0 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere

6.2: 0 - 20 °C / Inert atmosphere

7.1: Grubbs catalyst first generation / benzene / 2 h / Reflux; Inert atmosphere

8.1: water; N-bromoacetamide / 1,4-dioxane / 4 h / 20 °C / Inert atmosphere

9.1: sodium hydroxide / 1,4-dioxane / 0.5 h / 0 - 20 °C / Inert atmosphere

With Grubbs catalyst first generation; copper(l) iodide; (R,R)-Jacobsen catalyst; water; dihydrogen peroxide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; N-bromoacetamide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; benzene;

DOI:10.1016/j.tetasy.2011.05.012

upstream raw materials:

(2S)-2-benzhydryl-3,6-dihydro-2H-pyran

(2R)-2-benzhydryloxirane

(2S)-1,1-diphenylpent-4-en-2-ol

(S)-(2-(allyloxy)pent-4-ene-1,1-diyl)dibenzene

Downstream raw materials:

(3R,6S)-6-benzhydryltetrahydro-2H-pyran-3-ol

((3S,6S)-6-Benzhydryl-tetrahydro-pyran-3-yl)-(4-nitro-benzyl)-amine

(2S,4R,5R)-5-amino-2-benzhydryltetrahydro-2H-pyran-4-ol

cis-(3S,6S)-3-azido-6-benzhydryl-tetrahydropyran

Refernces

• 1、 Zhang, Shijun,Zhen, Juan,Reith, Maarten E. A.,Dutta, Aloke K.. "Discovery of novel trisubstituted asymmetric derivatives of (2S,4R,5R)-2-benzhydryl-5-benzylaminotetrahydropyran-4-ol, exhibiting high affinity for serotonin and norepinephrine transporters in a stereospecific manner". . p. 4962 - 4971. Retrieved 2007/10/03.