Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester
• CAS No.: 185312-46-3
• Molecular Formula: C₁₅H₁₇BrO₅
• Molecular Weight: 357.201
• Mol file: 185312-46-3.mol

Synonyms:Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester

Chemical Property of Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester

There total 2 articles about Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl 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: 95.0%

1,3'-di-O-benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanose (185312-45-2) → Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester (185312-46-3)

Guidance literature:

With trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1055/s-1996-4407

Reference yield:

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside (70147-50-1) → Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester (185312-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 95 percent / Me₃siBr, Me₃SiOTf / CH₂Cl₂ / 20 h / Ambient temperature

With pyridine; trimethylsilyl bromide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1055/s-1996-4407

Reference yield:

(E)-methyl 3-cyanoacrylate (925-56-4) + Benzoic acid (3aR,6S,6aR)-6-bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester (185312-46-3) → Benzoic acid (3aS,6S,6aS)-6-(1-cyano-2-methoxycarbonyl-ethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester + Benzoic acid (3aS,6S,6aS)-6-(2-cyano-1-methoxycarbonyl-ethyl)-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; In benzene; for 2.5h; Yield given. Yields of byproduct given; Heating;

DOI:10.1007/BF00807603

upstream raw materials:

1,3'-di-O-benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanose

3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside