Cyclopropanecarboxylic acid, 2-(hydroxymethyl)-3-phenyl-, 1,1-dimethylethyl ester, (1R,2S,3S)-

Base Information

Chemical Name:Cyclopropanecarboxylic acid, 2-(hydroxymethyl)-3-phenyl-, 1,1-dimethylethyl ester, (1R,2S,3S)-
CAS No.:392655-82-2
Molecular Formula:C15H20O3
Molecular Weight:248.322
Hs Code.:
Mol file:392655-82-2.mol

Synonyms:

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Chemical Property of Cyclopropanecarboxylic acid, 2-(hydroxymethyl)-3-phenyl-, 1,1-dimethylethyl ester, (1R,2S,3S)-

Chemical Property:

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Technology Process of Cyclopropanecarboxylic acid, 2-(hydroxymethyl)-3-phenyl-, 1,1-dimethylethyl ester, (1R,2S,3S)-

There total 9 articles about Cyclopropanecarboxylic acid, 2-(hydroxymethyl)-3-phenyl-, 1,1-dimethylethyl ester, (1R,2S,3S)- 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: 77.0%

: 392655-81-1
(1R,2S,3S)-tert-butyl 2-acetoxymethyl-3-phenyl-cyclopropanecarboxylate

: 392655-82-2
(1R,2S,3S)-tert-butyl 2-hydroxymethyl-3-phenyl-cyclopropanecarboxylate

Guidance literature:: With potassium carbonate; In methanol; water; at 20 ℃;
DOI:10.1021/jo010728d

Reference yield:

: 4407-36-7
(2E)-3-phenyl-2-propen-1-ol

: 392655-82-2
(1R,2S,3S)-tert-butyl 2-hydroxymethyl-3-phenyl-cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 91 percent / 120 °C / 70 Torr

2: 83 percent / tosyl azide; tetrabutylammonium bromide; aq. NaOH / CH₂Cl₂ / 20 °C

3: 44 percent / CuSO₄; Cu(aca)2 / benzene / Heating

4: 95 percent / LiAlH₄ / tetrahydrofuran / 20 °C

5: 97 percent / Pseudomonas fluorescens lipase AK / benzene / 4 h / 20 °C

6: 1.14 g / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.45 g / NaClO₂; NH₂SO₃H / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

8: 0.96 g / boron trifluoride diethyl etherate / CH₂Cl₂; cyclohexane / 0.5 h / 20 °C

9: 77 percent / K₂CO₃ / methanol; H₂O / 20 °C

With sodium hydroxide; sodium chlorite; lithium aluminium tetrahydride; 4-toluenesulfonyl azide; oxalyl dichloride; Cu(aca)2; Pseudomonas fluorescens lipase AK; boron trifluoride diethyl etherate; aminosulfonic acid; tetrabutylammomium bromide; potassium carbonate; copper(II) sulfate; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; tert-butyl alcohol; benzene; 6: Swern oxidation;
DOI:10.1021/jo010728d

Reference yield:

: 248936-93-8
1α,2α,3β-3-phenyl-1,2-cyclopropanedimethanol

: 392655-82-2
(1R,2S,3S)-tert-butyl 2-hydroxymethyl-3-phenyl-cyclopropanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / Pseudomonas fluorescens lipase AK / benzene / 4 h / 20 °C

2: 1.14 g / oxalyl chloride; dimethyl sulfoxide / CH₂Cl₂ / 0.5 h / -78 °C

3: 1.45 g / NaClO₂; NH₂SO₃H / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

4: 0.96 g / boron trifluoride diethyl etherate / CH₂Cl₂; cyclohexane / 0.5 h / 20 °C

5: 77 percent / K₂CO₃ / methanol; H₂O / 20 °C

With sodium chlorite; oxalyl dichloride; Pseudomonas fluorescens lipase AK; boron trifluoride diethyl etherate; aminosulfonic acid; potassium carbonate; dimethyl sulfoxide; In methanol; dichloromethane; cyclohexane; water; tert-butyl alcohol; benzene; 2: Swern oxidation;
DOI:10.1021/jo010728d