(1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide

Base Information

• Chemical Name: (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide
• CAS No.: 41348-33-8
• Molecular Formula: C₁₀H₁₆O₃S
• Molecular Weight: 216.301
• Mol file: 41348-33-8.mol

Synonyms:(1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide

Chemical Property of (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide

There total 3 articles about (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.0^1,5]decane 3,3-dioxide 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: 82.0%

acryloyl chloride (814-68-6,25189-84-8) + (1S,2R)-(7,7-dimethyl-2-hydroxybicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester (247078-63-3) → (1S,2R,4R)-2-exo-acryloyloxybornane-10-sulfonate + phenyl acrylate (937-41-7) + (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.01,5]decane 3,3-dioxide (41348-33-8)

Guidance literature:

(1S,2R)-(7,7-dimethyl-2-hydroxybicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

acryloyl chloride; In tetrahydrofuran; hexane; at -10 - 20 ℃; for 13h;

Reference yield: 81.0%

(1S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester (108885-08-1) → phenyl (1S,2S,4R)-2-endo-hydroxybornane-10-sulfonate (1021299-41-1) + (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.01,5]decane 3,3-dioxide (41348-33-8) + (1S,2R)-(7,7-dimethyl-2-hydroxybicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester (247078-63-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; water; at -8 ℃; for 16h;

Reference yield:

(1S,4R)-methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonate (62319-13-5) → (1S,2R,4R)-methyl (2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-yl)methanesulfonate + (1S,5R,7R)-10,10-dimethyl-4-oxa-3-thiatricyclo[5.2.1.01,5]decane 3,3-dioxide (41348-33-8)

Guidance literature:

(1S,4R)-methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonate; With sodium tetrahydroborate; In methanol;

With potassium tert-butylate; In methanol; Solvent;

DOI:10.1016/j.tetasy.2014.06.016

upstream raw materials:

(1S)-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester

acryloyl chloride

(1S,2R)-(7,7-dimethyl-2-hydroxybicyclo[2.2.1]hept-1-yl)methane sulfonic acid phenyl ester

(1S,4R)-methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonate

Downstream raw materials:

(1S)-(+)-10-(phenylsulfonyl)isoborneol

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

(1S)-10-(phenylsulfonyl)isobornyl bromoacetate

10-phenylsulfonylisobornyl chloroacetate