t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate

Base Information

• Chemical Name: t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate
• CAS No.: 877762-68-0
• Molecular Formula: C₂₂H₂₉NO₈
• Molecular Weight: 435.474

Synonyms:t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate

Chemical Property of t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate

Chemical Property:

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Technology Process of t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate

There total 2 articles about t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate 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: 86.0%

t-butyl [(3aS,5R,6aR)-5-((R)-1-hydroxypropyl)hexahydrofuro[2,3-b]furan-2-yl]acetate + 4-nitro-benzoic acid (62-23-7) → t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate (877762-68-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2005.10.078

Reference yield:

t-butyl {(3aS,5R,6aR)-5-[(R)-1-(t-butyldiphenylsilyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate → t-butyl {(2S,3aS,5R,6aR)-5-[(S)-1-(p-nitrobenzoyloxy)propyl]hexahydrofuro[2,3-b]furan-2-yl}acetate (877762-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TBAF / tetrahydrofuran / 48 h / 20 °C

2: 86 percent / diethyl azodicarboxylate; PPh₃ / 3 h / 20 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.10.078

upstream raw materials:

4-nitro-benzoic acid

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