cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate

Base Information

• Chemical Name: cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate
• CAS No.: 1472-00-0
• Molecular Formula: C₂₀H₂₄O₇S₂
• Molecular Weight: 440.538
• Mol file: 1472-00-0.mol

Synonyms:cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate

Chemical Property of cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate

There total 7 articles about cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + cis-tetrahydrofuran-2,5-dicarboxylic acid (2240-81-5) → cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate (1472-00-0)

Guidance literature:

With pyridine; for 12h; Ambient temperature;

DOI:10.1021/jo00133a038

Reference yield: 55.0%

cis-2,5-bis(hydroxymethyl)tetrahydrofuran (2144-40-3) + p-toluenesulfonyl chloride (98-59-9) → cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate (1472-00-0)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 0 - 20 ℃;

Reference yield:

(5S)-2,5-bis-(hydroxymethyl)tetrahydrofuran + p-toluenesulfonyl chloride (98-59-9) → (+)-(2S,5S)-trans-2,5-bis(tosylmethyl)tetrahydrofuran (81371-00-8) + cis-2,5-bis(hydroxymethyl)-tetrahydrofuran ditosylate (1472-00-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; Overall yield = 92 %; Overall yield = 922 mg; Inert atmosphere;

upstream raw materials:

cis-2,5-bis(hydroxymethyl)tetrahydrofuran

p-toluenesulfonyl chloride

cis-tetrahydrofuran-2,5-dicarboxylic acid

5-hydroxymethyl-2-furfuraldehyde

Downstream raw materials:

2,5-dioxohexane-1,6-diyl bis(4-methylbenzenesulfonate)

3-benzyl-8-oxa-3-aza-bicyclo[3.2.1]octane

8-oxabicyclo[3.2.1]octane-3-carboxylic acid

(1R,3S,5S)-3-[4-(4-Fluoro-phenoxy)-benzenesulfonylamino]-8-oxa-bicyclo[3.2.1]octane-3-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "3-(5-HYDROXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF". Paragraph 1390-1391. . Retrieved 2020/02/05.
• 2、 -. "THIENOPYRIMIDINE AND PYRAZOLOPYRIMIDINE COMPOUNDS AND THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS". Page/Page column 63. . Retrieved 2009/04/24.