(Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Base Information

• Chemical Name: (Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester
• CAS No.: 324027-22-7
• Molecular Formula: C₃₃H₃₁O₅P
• Molecular Weight: 538.58

Synonyms:(Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Chemical Property of (Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

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Technology Process of (Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

There total 3 articles about (Triphenyl-λ⁵-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl 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: 81.0%

triphenylphosphine (603-35-0) + Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (399534-53-3) → (Triphenyl-λ5-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (324027-22-7)

Guidance literature:

With sodium hydroxide; In benzene; for 15h; Heating;

DOI:10.1021/ol006651h

Reference yield:

benzyl bromide (100-39-0) → (Triphenyl-λ5-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (324027-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / NaH / dimethylformamide / 15 h / 20 °C

2: 84 percent / pyridine / CHCl₃ / 12 h / 20 °C

3: 81 percent / NaOH / benzene / 15 h / Heating

With pyridine; sodium hydroxide; sodium hydride; In chloroform; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ol006651h

Reference yield:

benzyl bromide (100-39-0) → (Triphenyl-λ5-phosphanylidene)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (324027-22-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 12 h

2: aq. NaOH

With pyridine; sodium hydroxide;

DOI:10.1016/j.tetasy.2003.07.006

upstream raw materials:

triphenylphosphine

Chloro-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

benzyl bromide

Downstream raw materials:

(E)-7-Oxo-hept-2-enoic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

((1R,2S)-2-Hydroxy-cyclopentyl)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

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