(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Base Information

• Chemical Name: (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate
• CAS No.: 186488-54-0
• Molecular Formula: C₁₃H₁₃NO₆
• Molecular Weight: 279.249
• Mol file: 186488-54-0.mol

Synonyms:(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Chemical Property of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate

There total 12 articles about (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 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: 99.0%

4-nitro-benzoic acid (62-23-7) + (3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan (252873-50-0) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate (186488-54-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at -10 - 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201200898

Reference yield: 92.0%

(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol (156928-09-5) + 4-nitro-benzoic acid (62-23-7) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate (186488-54-0)

Guidance literature:

With pyridine; triethylamine; at 0 - 20 ℃;

Reference yield:

γ-benzyloxymethyl-α,β-butenolide (72605-53-9) → (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate (186488-54-0)

Guidance literature:

Multi-step reaction with 5 steps

1: benzophenone / 9 h / 0 °C / UV-irradiation

2: 89 percent / H₂ / Pd/C / methanol / 24 h / 23 °C

3: LiAlH₄ / tetrahydrofuran / 4 h / 0 °C

4: 145 mg / HCl / tetrahydrofuran; H₂O / 40 h / 23 °C / pH 2 - 3

5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C

With hydrogenchloride; lithium aluminium tetrahydride; benzophenone; di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; benzene; 5: Mitsunobu reaction;

DOI:10.1021/jo049156y

upstream raw materials:

4-nitro-benzoic acid

(3S,3aS,6aR)-3-hydroxyhexahydrofuro[2,3-b]furan

γ-benzyloxymethyl-α,β-butenolide

(5S)-5-(hydroxymethyl)-5H-furan-2-one