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

Base Information

Chemical Name:1-Cyclopentene-1-carboxylic acid, 2-hydroxy-3-methoxy-5-methyl-4-(phenylmethoxy)-5-(2-propenyl)-, methyl ester, (3R,4S,5R)-
CAS No.:847845-23-2
Molecular Formula:C19H24O5
Molecular Weight:332.397
Hs Code.:

Synonyms:

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

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

There total 13 articles about 1-Cyclopentene-1-carboxylic acid, 2-hydroxy-3-methoxy-5-methyl-4-(phenylmethoxy)-5-(2-propenyl)-, methyl ester, (3R,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: 89.0%

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

: 847845-23-2
(3R,4S,5R)-5-allyl-4-benzyloxy-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-ene-1-carboxylic acid methyl ester

Guidance literature:: With dmap; pyridinium trifluroacetate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dimethyl sulfoxide;
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

: 847845-23-2
(3R,4S,5R)-5-allyl-4-benzyloxy-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-ene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 13 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

13.1: 89 percent / EDC; Py*TFA; DMAP / dimethylsulfoxide

With 1H-imidazole; dmap; potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile); Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 8.1: Tamao-Fleming oxidation / 13.1: Moffatt 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

: 847845-23-2
(3R,4S,5R)-5-allyl-4-benzyloxy-2-hydroxy-3-methoxy-5-methyl-cyclopent-1-ene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 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

11.1: 89 percent / EDC; Py*TFA; DMAP / dimethylsulfoxide

With 1H-imidazole; dmap; potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile); Grubbs catalyst first generation; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 6.1: Tamao-Fleming oxidation / 11.1: Moffatt oxidation;
DOI:10.1016/j.tetlet.2004.12.063