2,5-Methano-4H,5H-pyrano[2,3-d]-1,3- dioxin-6-carboxylic acid,4a,8a-dihydro-4-methyl-,methyl ester,(2R,4S,4aS,5S,8aR)-

Base Information

• Chemical Name: 2,5-Methano-4H,5H-pyrano[2,3-d]-1,3- dioxin-6-carboxylic acid,4a,8a-dihydro-4-methyl-,methyl ester,(2R,4S,4aS,5S,8aR)-
• CAS No.: 59653-37-1
• Molecular Formula: C11H14O5
• Molecular Weight: 226.2259
• Mol file: 59653-37-1.mol

Synonyms:Sarrancenia flava Extract;(+/-)-sarracenin;

Chemical Property of 2,5-Methano-4H,5H-pyrano[2,3-d]-1,3- dioxin-6-carboxylic acid,4a,8a-dihydro-4-methyl-,methyl ester,(2R,4S,4aS,5S,8aR)-

Chemical Property:

• Vapor Pressure: 0.000278mmHg at 25°C
• Boiling Point: 322.5°Cat760mmHg
• Flash Point: 142.1°C
• PSA: 53.99000
• Density: 1.262g/cm³
• LogP: 0.79710

Purity/Quality:

Analysis control,HPLC≥98% ^*data from raw suppliers

Sarracenin ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,5-Methano-4H,5H-pyrano[2,3-d]-1,3- dioxin-6-carboxylic acid,4a,8a-dihydro-4-methyl-,methyl ester,(2R,4S,4aS,5S,8aR)-

There total 25 articles about 2,5-Methano-4H,5H-pyrano[2,3-d]-1,3- dioxin-6-carboxylic acid,4a,8a-dihydro-4-methyl-,methyl ester,(2R,4S,4aS,5S,8aR)- 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: 61.0%

(7R,8R,9S)-9-(Toluene-4-sulfonyloxymethyl)-2,4,10-trioxa-tricyclo[5.3.1.03,8]undec-5-ene-6-carboxylic acid methyl ester (80325-29-7) → (+)-Sarracenin (25406-65-9,57456-76-5,59653-37-1,65914-07-0,78392-14-0,80374-30-7)

Guidance literature:

With sodium tetrahydroborate; In dimethyl sulfoxide; at 90 ℃; for 1.5h;

Reference yield: 31.0%

methyl (+/-)-<1R*,5S*,7R*,9S*(S*)>-7-hydroxy-9-(1-methoxyethyl)-2,8-dioxabicyclo<3.1.1>non-3-ene-4-carboxylate (118598-33-7) → (+/-)-sarracenin (25406-65-9,57456-76-5,59653-37-1,65914-07-0,78392-14-0,80374-30-7)

Guidance literature:

With boron tribromide; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1021/jo00264a034

Reference yield:

→ (+/-)-sarracenin (25406-65-9,57456-76-5,59653-37-1,65914-07-0,78392-14-0,80374-30-7)

Guidance literature:

With ozone; acetic acid; zinc; Multistep reaction; 1.) methylene chloride, -78 deg C, 2.) room temperature, 70 min; 70 deg C, 1 h;

DOI:10.1021/ja00402a035

upstream raw materials:

(4S,5S,6S)-4-Allyl-2-dimethylamino-6-methyl-5-vinyl-tetrahydro-pyran-3-carboxylic acid methyl ester; hydrochloride

(7R,8R,9S)-9-(Toluene-4-sulfonyloxymethyl)-2,4,10-trioxa-tricyclo[5.3.1.0^3,8]undec-5-ene-6-carboxylic acid methyl ester

(7R,8R,9S)-9-Hydroxymethyl-2,4,10-trioxa-tricyclo[5.3.1.0^3,8]undec-5-ene-6-carboxylic acid methyl ester

(7R,8R,9S)-9-Acetoxymethyl-2,4,10-trioxa-tricyclo[5.3.1.0^3,8]undec-5-ene-6-carboxylic acid methyl ester

Refernces

• 1、 Hoye, Thomas R.,Richardson, Wendy S.. "A Short, Oxetane-Based Synthesis of (+/-)-Sarracenin". . p. 688 - 693. Retrieved 2007/10/02.
• 2、 Tietze, Lutz-F.,Gluesenkamp, Karl-Heinz,Nakane, Masami,Hutchinson, C. Richard. "Stereokontrollierte Synthese von (+)-Sarracenin durch photochemische Cycloaddition". . p. 81 - 82. Retrieved 2007/10/02.