Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester
CAS No.:157523-16-5
Molecular Formula:C₁₃H₁₄O₅S
Molecular Weight:282.317
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

There total 8 articles about Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester 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: 86.0%

: 98-59-9
p-toluenesulfonyl chloride

: 159950-59-1
(1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.1.0]hexan-2-one

: 157523-16-5
Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Guidance literature:: With pyridine;
DOI:10.1016/0957-4166(94)80074-X

Reference yield: 54.0%

: 157523-15-4
2-tosyloxymethyl-7-oxa-2,3-diazabicyclo<3.3.0>oct-2-en-8-one

: 157523-16-5
Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Guidance literature:: In dichloromethane; for 2h; Irradiation;
DOI:10.1039/P19940001503

Reference yield:

: 78508-96-0
(5S)-5-(hydroxymethyl)-5H-furan-2-one

: 157523-16-5
Toluene-4-sulfonic acid (1S,2S,5R)-4-oxo-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / DMAP

2: 11.1 g / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

3: 86 percent / toluene / 2.5 h / -78 °C / Irradiation

4: 98 percent / n-Bu₄NF / tetrahydrofuran / 0.17 h / Ambient temperature

5: 86 percent / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo972219a