3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(9CI)

Base Information

• Chemical Name: 3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(9CI)
• CAS No.: 90687-25-5
• Molecular Formula: C₈H₁₀O₄
• Molecular Weight: 170.165
• Mol file: 90687-25-5.mol

Synonyms:3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(9CI)

Chemical Property of 3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(9CI)

There total 4 articles about 3-Oxatricyclo[2.2.1.02,6]heptane-1-carboxylicacid,5-hydroxy-,methylester(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: 63.0%

exo-2,3-epoxy-6-methoxycarbonyl-7-oxabicyclo<2.2.1>heptane (81763-39-5,81800-81-9,92936-00-0,92936-01-1) → 3-hydroxy-6-methoxycarbonyl-7-oxa-tricyclo<2.2.1.02,6>heptane (90687-25-5,90762-16-6)

Guidance literature:

With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)83498-0

Reference yield:

exo-2,3-epoxy-6-methoxycarbonyl-7-oxabicyclo<2.2.1>heptane (81763-39-5,81800-81-9,92936-00-0,92936-01-1) → (1S,2S,4S,5R,6R)-5-Hydroxy-3-oxa-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid methyl ester (90687-25-5,90762-16-6) + methyl cis-3,4-epoxy-5-hydroxy-cyclohexene-1-carboxylate (78844-86-7,78961-89-4,83648-86-6,90866-42-5,90866-43-6)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃; Yield given;

Reference yield:

7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester (17791-32-1,17791-33-2,21987-33-7,88517-51-5,88517-52-6,204988-60-3) → (1S,2S,4S,5R,6R)-5-Hydroxy-3-oxa-tricyclo[2.2.1.02,6]heptane-1-carboxylic acid methyl ester (90687-25-5,90762-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: MCPBA

2: LDA / -78 °C

With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;

upstream raw materials:

exo-2,3-epoxy-6-methoxycarbonyl-7-oxabicyclo<2.2.1>heptane

7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester