(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

Base Information

Chemical Name:(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene
CAS No.:856258-22-5
Molecular Formula:C₂₉H₃₇NO₆
Molecular Weight:495.616
Hs Code.:

Synonyms:(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

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Chemical Property of (1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

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Technology Process of (1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

There total 4 articles about (1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene 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: 97.0%

: 856258-21-4
(1S,5S,1'S,2'S)-5-[1-tert-butoxycarbonylamino-2,3-bis(benzyloxy)propyl]cyclopent-2-en-1-ol

: 108-24-7
acetic anhydride

: 856258-22-5
(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

Guidance literature:: With pyridine; dmap; for 16h;
DOI:10.1021/ol0504493

Reference yield:

: 1-(4,6a-dihydro-3aH-cyclopenta[d]isoxazol-3-yl)-ethane-1,2-diol

: 856258-22-5
(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: 687 mg / NaH / dimethylformamide / 4 h

2.1: LiAlH₄ / diethyl ether / 1.5 h / Heating

2.2: 78 percent / dioxane; H₂O / 16 h / 20 °C

3.1: 97 percent / pyridine; DMAP / 16 h

With pyridine; dmap; lithium aluminium tetrahydride; sodium hydride; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ol0504493

Reference yield:

: (1'S)-3-(1,2-O-isopropylidenedioxyethyl)-4,6a-dihydro-3aH-cyclopenta[d]isoxazole

: 856258-22-5
(1S,5S,1'S,2'S)-1-acetoxy-5-[2,3-bis(benzyloxy)-1-tert-butoxycarbonylaminopropyl]cyclopent-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / CF₃COOH / methanol; H₂O

2.1: 687 mg / NaH / dimethylformamide / 4 h

3.1: LiAlH₄ / diethyl ether / 1.5 h / Heating

3.2: 78 percent / dioxane; H₂O / 16 h / 20 °C

4.1: 97 percent / pyridine; DMAP / 16 h

With pyridine; dmap; lithium aluminium tetrahydride; sodium hydride; trifluoroacetic acid; In methanol; diethyl ether; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0504493