Cyclopentanecarboxylic acid, 5-hydroxy-4-methoxy-2-methyl-3-(phenylmethoxy)-2-(2-propenyl)-, methyl ester, (1R,2R,3S,4S,5R)-

Base Information

Chemical Name:Cyclopentanecarboxylic acid, 5-hydroxy-4-methoxy-2-methyl-3-(phenylmethoxy)-2-(2-propenyl)-, methyl ester, (1R,2R,3S,4S,5R)-
CAS No.:847845-10-7
Molecular Formula:C19H26O5
Molecular Weight:334.412
Hs Code.:

Synonyms:

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Chemical Property of Cyclopentanecarboxylic acid, 5-hydroxy-4-methoxy-2-methyl-3-(phenylmethoxy)-2-(2-propenyl)-, methyl ester, (1R,2R,3S,4S,5R)-

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Technology Process of Cyclopentanecarboxylic acid, 5-hydroxy-4-methoxy-2-methyl-3-(phenylmethoxy)-2-(2-propenyl)-, methyl ester, (1R,2R,3S,4S,5R)-

There total 13 articles about Cyclopentanecarboxylic acid, 5-hydroxy-4-methoxy-2-methyl-3-(phenylmethoxy)-2-(2-propenyl)-, methyl ester, (1R,2R,3S,4S,5R)- 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:

: (1R,2R,3S,4R,5R)-2-Allyl-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-2-methyl-cyclopentanecarboxylic acid methyl ester

: 847845-10-7
(1R,2R,3S,4S,5R)-2-allyl-3-benzyloxy-5-hydroxy-4-methoxy-2-methyl-cyclopentane-1-carboxylic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2004.12.063

Reference yield:

: 1046780-06-6
(3R,4S,5R)-3-Benzyloxy-4-methoxy-5-vinyl-dihydro-furan-2-one

: 847845-10-7
(1R,2R,3S,4S,5R)-2-allyl-3-benzyloxy-5-hydroxy-4-methoxy-2-methyl-cyclopentane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: tetrahydrofuran / -78 °C

2.1: 54 percent / imidazole / dimethylformamide

3.1: 98 percent / TiCl₄ / tetrahydrofuran / 0 - 20 °C

4.1: 90 percent / Grubbs' catalyst / benzene / 80 °C

5.1: 80 percent / TBAF / tetrahydrofuran

6.1: 80 percent / DMAP; Et₃N / CH₂Cl₂

7.1: 1,1'-azobis(cyclohexanecarbonitrile) / heptane / 24 h / 100 °C

8.1: H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 80 °C

9.1: 92 percent / imidazole / dimethylformamide

10.1: PPTS / ethanol

10.2: DMP; pyridine / CH₂Cl₂

10.3: NaClO₂; KH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s)

11.1: benzene; methanol

12.1: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium hydrogencarbonate; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile); Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; benzene; 8.1: Tamao-Fleming oxidation;
DOI:10.1016/j.tetlet.2004.12.063

Reference yield:

: 847845-05-0
(3R,4R,5R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-hept-6-en-2-one

: 847845-10-7
(1R,2R,3S,4S,5R)-2-allyl-3-benzyloxy-5-hydroxy-4-methoxy-2-methyl-cyclopentane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / TiCl₄ / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / Grubbs' catalyst / benzene / 80 °C

3.1: 80 percent / TBAF / tetrahydrofuran

4.1: 80 percent / DMAP; Et₃N / CH₂Cl₂

5.1: 1,1'-azobis(cyclohexanecarbonitrile) / heptane / 24 h / 100 °C

6.1: H₂O₂; KF; KHCO₃ / methanol; tetrahydrofuran / 80 °C

7.1: 92 percent / imidazole / dimethylformamide

8.1: PPTS / ethanol

8.2: DMP; pyridine / CH₂Cl₂

8.3: NaClO₂; KH₂PO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s)

9.1: benzene; methanol

10.1: TBAF / tetrahydrofuran

With 1H-imidazole; dmap; potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium hydrogencarbonate; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile); Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; benzene; 6.1: Tamao-Fleming oxidation;
DOI:10.1016/j.tetlet.2004.12.063