(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

Base Information

Chemical Name:(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol
CAS No.:347377-76-8
Molecular Formula:C₂₈H₂₅NO₇
Molecular Weight:487.509
Hs Code.:

Synonyms:(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

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Chemical Property of (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

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Technology Process of (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

There total 8 articles about (+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol 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: 84.0%

: 3173-56-6
benzyl isothiocyanate

: 347377-81-5
(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-5-cyclohexene-2,3-diol

: 347377-76-8
(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

: C₃₆H₃₂N₂O₈

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1002/1521-3765(20010417)7:8<1619::AID-CHEM16190>3.0.CO;2-4

Reference yield:

: 5273-61-0,14624-09-0,112212-80-3
(5RS,6RS)-5,6-dibromocyclohex-2-ene-1,4-dione

: 347377-76-8
(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / NaBH₄ / diethyl ether; H₂O

2.1: K₂CO₃ / 0 - 20 °C

2.2: 71 percent / Heating

3.1: 100 percent / NEt₃; H₂O / methanol

4.1: 90 percent / pyridine; DMAP / CH₂Cl₂

5.1: 90 percent / aq. NaOH; tetrahexylammonium bromide; (1S,2S)-1,2-[o-(PPh2)C6H4CONH]2-cyclohexane / [η³-C3H5)PdCl]2 / CH2Cl2 / 18 h / 20 °C

6.1: 77 percent / Zn; AcOH / tetrahydrofuran / 2 h / 20 °C

7.1: 84 percent / NEt₃ / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; dmap; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium hydroxide; sodium tetrahydroborate; water; tetrahexylammonium bromide; potassium carbonate; acetic acid; triethylamine; zinc; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1002/1521-3765(20010417)7:8<1619::AID-CHEM16190>3.0.CO;2-4

Reference yield:

: 526-87-4,4782-74-5,4782-75-6,4782-76-7,4942-61-4,4942-62-5,6090-98-8,7586-48-3,25348-64-5,80338-90-5,123238-09-5,129829-50-1,129829-51-2,133319-93-4,137567-79-4,138258-55-6,139559-64-1,140923-39-3
(+/-)-Conduritol B

: 347377-76-8
(+)-(1S,2R,3R,4S)-1,4-Dibenzoyloxy-2-(N-benzyl)carbamyl-5-cyclohexene-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / pyridine; DMAP / CH₂Cl₂

2: 90 percent / aq. NaOH; tetrahexylammonium bromide; (1S,2S)-1,2-[o-(PPh2)C6H4CONH]2-cyclohexane / [η³-C3H5)PdCl]2 / CH2Cl2 / 18 h / 20 °C

3: 77 percent / Zn; AcOH / tetrahydrofuran / 2 h / 20 °C

4: 84 percent / NEt₃ / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; dmap; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium hydroxide; tetrahexylammonium bromide; acetic acid; triethylamine; zinc; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; dichloromethane;
DOI:10.1002/1521-3765(20010417)7:8<1619::AID-CHEM16190>3.0.CO;2-4