4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose

Base Information

• Chemical Name: 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose
• CAS No.: 123488-18-6
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381

Synonyms:4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose

Chemical Property of 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose

Chemical Property:

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Technology Process of 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose

There total 3 articles about 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose 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:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose (123488-18-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / diisopropylethylamine, LiCl / acetonitrile / 18 h

2: Pd(OAc)2, (i-C₃H₇O)3P / toluene / 18 h / 80 - 85 °C

With N-ethyl-N,N-diisopropylamine; lithium chloride; palladium diacetate; triisopropyl phosphite; In toluene; acetonitrile;

DOI:10.1021/ja00201a032

Reference yield:

3-O-Benzyl-5,6-dideoxy-(E)-5,6-didehydro-1,2-O-isopropylidene-α-D-gluco-1,4-furanose (123487-99-0) → 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose (123488-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd(OAc)2, (i-C₃H₇O)3P / toluene / 18 h / 80 - 85 °C

palladium diacetate; triisopropyl phosphite; In toluene;

DOI:10.1021/ja00201a032

Reference yield:

(3aR,5R,6S,6aR)-5-((1R,2S)-2-Benzenesulfonyl-4-methylene-cyclopentyl)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (123488-09-5) → 4-(1-Oxocyclopent-2-en-4S-yl)-1,2-O-isopropylidene-3-O-benzyl-α-D-threo-1,4-furanose (123488-18-6)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/ja00201a032

upstream raw materials:

(3aR,5R,6S,6aR)-5-((1R,2S)-2-Benzenesulfonyl-4-methylene-cyclopentyl)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

3-O-Benzyl-5,6-dideoxy-(E)-5,6-didehydro-1,2-O-isopropylidene-α-D-gluco-1,4-furanose

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

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