(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane
CAS No.:327620-54-2
Molecular Formula:C₁₄H₁₈O₃
Molecular Weight:234.295
Hs Code.:

Synonyms:(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

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Chemical Property of (1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

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Technology Process of (1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

There total 6 articles about (1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane 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: 70.0%

: 327620-53-1
3-phenylpropionic acid (2S)-2-(methyloxiranyl)ethyl ester

: 327620-54-2
(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

Guidance literature:: 3-phenylpropionic acid (2S)-2-(methyloxiranyl)ethyl ester; With silver perchlorate; zirconocene dichloride; In dichloromethane; at 0 ℃; for 4h;

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 10h; Further stages.;
DOI:10.1021/jo005665y

Reference yield:

: 6236-09-5,2306-22-1
(S)-citramalic acid

: 327620-54-2
(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂SO₄; MeOH

1.2: 72 percent / LAH / tetrahydrofuran

2.1: 81 percent / P₂O₅ / 15 h / 20 °C

3.1: 79 percent / DMAP; EDCI / CH₂Cl₂ / 15 h / 20 °C

4.1: 57 percent / pTsOH / tetrahydrofuran; H₂O / 4 h / Heating

5.1: MsCl; Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

5.2: 82 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

6.1: AgClO₄ / Cp₂ZrCl₂ / CH₂Cl₂ / 4 h / 0 °C

6.2: 70 percent / aq. LiOH / tetrahydrofuran / 10 h / 20 °C

With methanol; dmap; sulfuric acid; silver perchlorate; phosphorus pentoxide; toluene-4-sulfonic acid; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; zirconocene dichloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo005665y

Reference yield:

: 60299-29-8
(S)-(-)-2-Methylbutane-1,2,4-triol

: 327620-54-2
(1S,5R)-5-methyl-1-phenethyl-2,7,8-trioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 81 percent / P₂O₅ / 15 h / 20 °C

2.1: 79 percent / DMAP; EDCI / CH₂Cl₂ / 15 h / 20 °C

3.1: 57 percent / pTsOH / tetrahydrofuran; H₂O / 4 h / Heating

4.1: MsCl; Et₃N / CH₂Cl₂ / 0.33 h / -10 °C

4.2: 82 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

5.1: AgClO₄ / Cp₂ZrCl₂ / CH₂Cl₂ / 4 h / 0 °C

5.2: 70 percent / aq. LiOH / tetrahydrofuran / 10 h / 20 °C

With dmap; silver perchlorate; phosphorus pentoxide; toluene-4-sulfonic acid; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; zirconocene dichloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo005665y