(1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane

Base Information

• Chemical Name: (1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane
• CAS No.: 82398-68-3
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• European Community (EC) Number: 843-154-1
• Nikkaji Number: J973.592E,J973.593C
• Mol file: 82398-68-3.mol

Synonyms:82398-68-3;(1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane;(1R,3S,5S)-3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane;82353-76-2;(1alpha,5alpha)-3alpha-Benzyloxy-6-oxabicyclo[3.1.0]hexane;starbld0024700;SCHEMBL1438982;SCHEMBL1988191;SCHEMBL1988788;EN300-371824;EN300-373947;(1R,3r,5S)-3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane;Z2758800401;(1alpha,5alpha)-3beta-Benzyloxy-6-oxabicyclo[3.1.0]hexane

Chemical Property of (1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 189

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(CC2C1O2)OCC3=CC=CC=C3
• Isomeric SMILES: C1[C@@H]2[C@@H](O2)CC1OCC3=CC=CC=C3

Technology Process of (1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane

There total 14 articles about (1S,5R)-3-phenylmethoxy-6-oxabicyclo[3.1.0]hexane 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: 80.8%

[(cyclopent-3-en-1-yloxy)methyl]benzene (37005-79-1) → 3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane (82353-76-2,82398-68-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 2h;

Reference yield: 45.0%

[(cyclopent-3-en-1-yloxy)methyl]benzene (37005-79-1) → (1R,3r,5S)-3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane (82353-76-2) + (1R,3s,5S)-3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane (82398-68-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)00374-5

Reference yield:

cyclopent-3-enol (14320-38-8) → 3-(benzyloxy)-6-oxabicyclo[3.1.0]hexane (82353-76-2,82398-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: KH

2: m-CPBA / CH₂Cl₂

With potassium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/0957-4166(95)00158-L

upstream raw materials:

[(cyclopent-3-en-1-yloxy)methyl]benzene

cyclopent-3-enol

benzyl bromide

benzyl chloride

Downstream raw materials:

1-benzyloxyl-3-hydroxylcyclopentane

3-(benzyloxy)cyclopentan-1-one

C₁₇H₂₅NO₃

(1R,2R,4R)-2-azido-4-(benzyloxy)cyclopentyl methanesulfonate