Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester
• CAS No.: 114340-83-9
• Molecular Formula: C₂₀H₂₀O₆
• Molecular Weight: 356.375

Synonyms:Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester

There total 2 articles about Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-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: 58.0%

Benzoic acid (2R,3R,4S,5R)-4-benzyloxy-5-[1,3]dioxolan-2-yl-2-phenyl-tetrahydro-furan-3-yl ester (114340-82-8) → Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester (114340-83-9)

Guidance literature:

With trimethylsilyl iodide; In dichloromethane; for 48h; -20 deg C to +5 deg C;

DOI:10.1016/S0040-4039(00)96428-1

Reference yield:

(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dioxolan-2-yl-2-phenyl-tetrahydro-furan-3-ol (114340-81-7) → Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester (114340-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / pyridine / Ambient temperature

2: 53 percent / trimethylsilyl iodide / CH₂Cl₂ / 48 h / -20 - 5 °C

With trimethylsilyl iodide; In pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)80093-4

Reference yield: 90.0%

Benzoic acid (2R,3S,4S,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-2-phenyl-tetrahydro-furan-3-yl ester (114340-83-9) + benzoyl chloride (98-88-4) → (2R,3S,4R,5R)-3,4-dibenzoyloxy-5-phenyltetrahydrofuran-2-ethyleneacetal (114340-84-0)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/S0040-4020(01)80093-4

upstream raw materials:

Benzoic acid (2R,3R,4S,5R)-4-benzyloxy-5-[1,3]dioxolan-2-yl-2-phenyl-tetrahydro-furan-3-yl ester

(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dioxolan-2-yl-2-phenyl-tetrahydro-furan-3-ol

Downstream raw materials:

(2R,3S,4R,5R)-3,4-dibenzoyloxy-5-phenyltetrahydrofuran-2-ethyleneacetal

goniothalenol

(2R,3S,4R,5R)-2-(1'-oxomethyl)-3,4-dibenzoyloxy-5-phenyltetrahydrofuran

C₂₈H₂₄O₇

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