Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI)
• CAS No.: 615249-15-5
• Molecular Formula: C9H14O3
• Molecular Weight: 170.20566
• Mol file: 615249-15-5.mol

Synonyms:Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI)

Chemical Property of Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI)

Chemical Property:

• PSA: 77.76000
• LogP: 0.22900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI)

There total 8 articles about Bicyclo[2.2.1]heptane-2,5-diol, monoacetate, (1S,2S,4S,5R)- (9CI) 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: 95.0%

5-endo-Acetoxy-7-anti-phenylthiobicyclo<2.2.1>heptan-2-one (136713-26-3) → Acetic acid (1R,2R,4R)-5-hydroxy-bicyclo[2.2.1]hept-2-yl ester (35553-68-5,85201-75-8,85201-76-9,135094-35-8,135094-37-0,136779-73-2,147920-65-8,615249-15-5)

Guidance literature:

With nickel; In ethanol; for 1.5h; Heating;

Reference yield: 80.0%

exo,exo-2,5-Diacetoxybicyclo[2.2.1]heptane (5888-39-1,100162-32-1,134986-31-5,134986-32-6,135094-51-8,135094-52-9,146075-50-5) → exo,exo-5-acetoxybicyclo<2.2.1>heptan-2-ol (615249-15-5)

Guidance literature:

for 57h; Ambient temperature; porcine pancreatic lipase, Tris buffer, pH 7.1;

Reference yield:

endo-5-norbornen-2-yl acetate → 2-endo-6-exo-6-hydroxybicyclo[2.2.1]heptan-2-yl acetate (615249-16-6) + 2-endo-6-exo-6-hydroxybicyclo[2.2.1]heptan-2-yl acetate (615249-15-5)

Guidance literature:

endo-5-norbornen-2-yl acetate; With borane-THF; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 ℃; for 0.833333h; Overall yield = 7.79 g;

DOI:10.1016/j.tet.2013.09.071

upstream raw materials:

5-endo-Acetoxy-7-anti-phenylthiobicyclo<2.2.1>heptan-2-one

3-endo-Acetoxy-2-exo-bromobicyclo<3.2.0>heptan-6-one

(1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate

exo,exo-2,5-Diacetoxybicyclo[2.2.1]heptane