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

Base Information

Chemical Name:(Z)-7-[(1S,2S,3R,5R)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid methyl ester
CAS No.:130520-25-1
Molecular Formula:C₂₀H₂₇NO₅S
Molecular Weight:393.504
Hs Code.:

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

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

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

There total 22 articles about (Z)-7-[(1S,2S,3R,5R)-3-(Toluene-4-sulfonylamino)-6-oxa-bicyclo[3.1.0]hex-2-yl]-hept-5-enoic acid methyl 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:

: 26054-46-6
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

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

Guidance literature:: Multi-step reaction with 8 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

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:

: 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

: 130520-25-1
(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

Guidance literature:: Multi-step reaction with 8 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

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

: 130520-25-1
(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

Guidance literature:: Multi-step reaction with 9 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

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