Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Base Information

• Chemical Name: Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
• CAS No.: 140363-85-5
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.354

Synonyms:Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property of Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Chemical Property:

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Technology Process of Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

There total 2 articles about Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-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: 94.0%

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose (63598-38-9,167074-37-5) + pent-4-enoic acid (591-80-0) → 4,6-Di-O-benzylidene-3-O-(4-pentenoyl)-D-allal (140363-85-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00117a042

Reference yield: 94.0%

4,6-O-benzylidene-D-allal (5987-33-7,167074-37-5) + pent-4-enoic acid (591-80-0) → Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (140363-85-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1039/c39920000094

Reference yield: 57.0%

Pent-4-enoic acid (4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (140363-85-5) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → (4aR,8aS)-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine (140363-89-9,140460-24-8)

Guidance literature:

With iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; In dichloromethane;

DOI:10.1039/c39920000094

upstream raw materials:

4,6-O-benzylidene-D-allal

pent-4-enoic acid

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

Downstream raw materials:

Acetic acid (3S,4R,5R)-4-acetoxy-2,5-bis-acetoxymethyl-2-((4aR,6R,8aS)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-furan-3-yl ester

(4aR,8aS)-6-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

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