(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

Base Information

Chemical Name:(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester
CAS No.:267665-90-7
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

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Chemical Property of (4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

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Technology Process of (4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

There total 8 articles about (4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl 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: 78.0%

: 77-76-9
2,2-dimethoxy-propane

: 267665-89-4
(1R,3S)-3-((1S,2R)-3-Benzyloxy-1,2-dihydroxy-propyl)-2,2-dimethyl-cyclopropanecarboxylic acid methyl ester

: 267665-90-7
(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 1h;
DOI:10.1002/jccs.200000004

Reference yield:

: 22379-62-0
potassium benzyloxide

: 267665-90-7
(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran

1.2: KOH / tetrahydrofuran

1.3: 16 percent / methanol

2.1: 78 percent / p-TsOH / 1 h / 20 °C

With toluene-4-sulfonic acid; In tetrahydrofuran; 1.1: Ring cleavage / 1.2: saponification / 1.3: Methylation / 2.1: ketalization;
DOI:10.1002/jccs.200000004

Reference yield:

: 139727-13-2
(4S,5R)-2,2-Dimethyl-4-(2-methyl-1-propenyl)-5-(hydroxymethyl)-1,3-dioxolane

: 267665-90-7
(4R,5S,2'S,2'R)-2'(4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3',3'-dimethyl-cyclopropanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 91 percent / pyridine / 20 °C

2.1: 82 percent / 1 N aq. HCl / methanol / 20 °C

3.1: 88 percent / K₂CO₃ / methanol / 2 h / 0 °C

4.1: 86 percent / N,N-DMA; Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: 70 percent / Rh₂[(5S)-MEPY]4 / CH₂Cl₂ / 20 °C

6.1: tetrahydrofuran

6.2: KOH / tetrahydrofuran

6.3: 16 percent / methanol

7.1: 78 percent / p-TsOH / 1 h / 20 °C

With pyridine; hydrogenchloride; N,N-dimethyl acetamide; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Tosylation / 2.1: Hydrolysis / 3.1: Epoxidation / 4.1: Condensation / 5.1: Cyclization / 6.1: Ring cleavage / 6.2: saponification / 6.3: Methylation / 7.1: ketalization;
DOI:10.1002/jccs.200000004