Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

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Chemical Name:Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester
CAS No.:873014-41-6
Molecular Formula:C₃₄H₄₃NO₉S
Molecular Weight:641.783
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

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Chemical Property of Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

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Technology Process of Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

There total 5 articles about Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl 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: 65.0%

: 825633-62-3
[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

: 778-29-0
but-3-enyl 4-methylbenzenesulfonate

: 873014-41-6
Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

Guidance literature:: With RCM; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane;
DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

: 544455-38-1
ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

: 873014-41-6
Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / LiOH; (DHQD)2PHAL; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2.1: NaH / dimethylformamide / 10 h / 0 °C

2.2: DMAP / tetrahydrofuran / 4 h / Heating

2.3: NH₂NH₂ / methanol / 4 h

3.1: 90 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

4.1: tetrahydrofuran / 1 h / -50 °C

4.2: 85 percent / tetrahydrofuran / 1 h / 20 °C

5.1: 65 percent / RCM / Grubbs' second generation catalyst / CH₂Cl₂

With lithium hydroxide; potassium osmate(VI); sodium hydride; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

: 544455-39-2
(2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester

: 873014-41-6
Toluene-4-sulfonic acid (E)-(5S,6S,7R)-6-benzyloxy-7-tert-butoxycarbonylamino-5-hydroxy-8-(4-methoxy-phenoxy)-oct-3-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 10 h / 0 °C

1.2: DMAP / tetrahydrofuran / 4 h / Heating

1.3: NH₂NH₂ / methanol / 4 h

2.1: 90 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

3.1: tetrahydrofuran / 1 h / -50 °C

3.2: 85 percent / tetrahydrofuran / 1 h / 20 °C

4.1: 65 percent / RCM / Grubbs' second generation catalyst / CH₂Cl₂

With sodium hydride; diisobutylaluminium hydride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.10.074