[(2S,3R)-3-(methylsulfonyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl methanesulfonate

Base Information

• Chemical Name: [(2S,3R)-3-(methylsulfonyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl methanesulfonate
• CAS No.: 2590-37-6
• Molecular Formula: C₁₁H₁₈O₆S₂
• Molecular Weight: 310.392
• NSC Number: 81679,81678
• Mol file: 2590-37-6.mol

Synonyms:NSC81678;2590-37-6;NSC81679;NSC-81678;NSC-81679;2434-86-8

Chemical Property of [(2S,3R)-3-(methylsulfonyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl methanesulfonate

Chemical Property:

• Vapor Pressure: 2.99E-10mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 516.2°Cat760mmHg
• Flash Point: 266°C
• Density: 1.358g/cm³
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 310.05448064
• Heavy Atom Count: 19
• Complexity: 501

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)(=O)OCC1C2CC(C1COS(=O)(=O)C)C=C2
• Isomeric SMILES: CS(=O)(=O)OC[C@@H]1[C@@H](C2CC1C=C2)COS(=O)(=O)C

Technology Process of [(2S,3R)-3-(methylsulfonyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl methanesulfonate

There total 7 articles about [(2S,3R)-3-(methylsulfonyloxymethyl)-2-bicyclo[2.2.1]hept-5-enyl]methyl methanesulfonate 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: 97.0%

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol (941567-71-1,448922-61-0) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (1S,2R,3S,4R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (2434-86-8,2434-87-9,77983-96-1,91967-21-4,2590-37-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jacs.7b11960

Reference yield: 88.0%

methanesulfonyl chloride (124-63-0) + trans-5-norbornene-2,3-dimethanol (85-39-2,699-95-6,699-96-7,699-97-8,54423-36-8,78037-77-1,79516-58-8,111321-65-4,448922-61-0) → Methanesulfonic acid (2R,3R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (2434-86-8,2434-87-9,2590-37-6,77983-96-1,91967-21-4)

Guidance literature:

at 0 ℃; for 8h;

DOI:10.1021/ja00404a028

Reference yield:

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → Methanesulfonic acid (1S,2R,3S,4R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester (2434-86-8,2434-87-9,77983-96-1,91967-21-4,2590-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 5.5 h / 20 °C

2: 83 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo0620260

upstream raw materials:

bicyclo<2.2.1>-5-hepten-2endo,3endo-dicarboxylic anhydride

methanesulfonyl chloride

(1R,2S,3R,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dimethanol

3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

exo-9-oxa-endo-4-thiatricyclo<5.2.1.0^2,6>decane-4,4-dioxide

endo-4-thiatricyclo<5.2.1.0^2,6>dec-8-ene 4,4-dioxide

(1S,7R)-4-Thia-tricyclo[5.2.1.0^2,6]dec-8-ene 4,4-dioxide

1-((1R,3S,7S)-4,4-Dioxo-4λ⁶-thia-tricyclo[5.2.1.0^2,6]dec-8-en-3-yl)-cyclohexanol