(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

Base Information

Chemical Name:(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid
CAS No.:130520-26-2
Molecular Formula:C₁₉H₂₅NO₅S
Molecular Weight:379.477
Hs Code.:

Synonyms:(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

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Chemical Property of (Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

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Technology Process of (Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

There total 13 articles about (Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid 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: 96.0%

: 130520-25-1
(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid methyl ester

: 130520-26-2
(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; water; at 23 ℃; for 4h;
DOI:10.1016/S0040-4039(00)97481-1

Reference yield:

: 34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6
(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 130520-26-2
(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: LiOH / methanol; H₂O; tetrahydrofuran / 2 h / 23 °C

2: diethyl ether

3: Mitsunobu reaction

4: 96 percent / TFA / CH₂Cl₂ / 24 h / 23 °C

6: 99 percent / K₂CO₃ / 1 h / 23 °C

7: DIBAH / hexane; toluene / -78 °C

8: 1) sodium hexamethyldisilazane / 1) toluene, THF, -40 to 0 deg C, 2 h 2) 0 deg C

9: 96 percent / LiOH / methanol; H₂O; tetrahydrofuran / 4 h / 23 °C

With lithium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1016/S0040-4039(00)97481-1

Reference yield:

: 71155-04-9
(1S,5R)-(-)-bicyclo[3.2.0]hept-2-en-6-one

: 130520-26-2
(Z)-7-[(1R,2R,3S,5S)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / 30percent H₂O₂, HOAc / 12 h / 0 °C

2: LiOH / methanol; H₂O; tetrahydrofuran / 2 h / 23 °C

3: diethyl ether

4: Mitsunobu reaction

5: 96 percent / TFA / CH₂Cl₂ / 24 h / 23 °C

7: 99 percent / K₂CO₃ / 1 h / 23 °C

8: DIBAH / hexane; toluene / -78 °C

9: 1) sodium hexamethyldisilazane / 1) toluene, THF, -40 to 0 deg C, 2 h 2) 0 deg C

10: 96 percent / LiOH / methanol; H₂O; tetrahydrofuran / 4 h / 23 °C

With lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene;
DOI:10.1016/S0040-4039(00)97481-1