(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Base Information

Chemical Name:(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester
CAS No.:259199-02-5
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

There total 8 articles about (Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic 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: 73.0%

: 88738-78-7
bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

: 259199-01-4
{(2R)-6-[3-(4-methoxybenzyloxy)-2-methyl-propyl]-(2R,6S)-5,6-dihydro-2H-pyran-2-yl}acetaldehyde

: 259199-02-5
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

: (E)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(99)02021-3

Reference yield:

: 136320-64-4
(2R)-3-[(4-methoxybenzyl)oxy]-2-methylpropanol

: 259199-02-5
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 20 °C

2: dimethylsulfoxide / 80 °C

3: 80 percent / DIBAH / tetrahydrofuran / -78 - 20 °C

4: 90 percent / diethyl ether / -100 °C

5: 84 percent / PPTS / toluene / 35 °C / 60 Torr

6: 94 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / Heating

7: 81 percent / montmorillonite K-10 / CH₂Cl₂ / 20 °C

8: 73 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

With pyridine; Grubbs catalyst first generation; 18-crown-6 ether; montmorillonite K-10; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; 1: Tosylation / 2: Substitution / 3: Reduction / 4: modified Brown allylation / 5: transketalization / 6: Cyclization / 7: Alkylation / 8: Alkylation;
DOI:10.1016/S0040-4039(99)02021-3

Reference yield:

: 259198-97-5
(3R)-4-(4-methoxybenzyloxy)-3-methylbutyraldehyde

: 259199-02-5
(Z)-4-{(2R,6S)-6-[(R)-3-(4-Methoxy-benzyloxy)-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / diethyl ether / -100 °C

2: 84 percent / PPTS / toluene / 35 °C / 60 Torr

3: 94 percent / Cl₂(Cy₃P)2Ru=CHPh / CH₂Cl₂ / Heating

4: 81 percent / montmorillonite K-10 / CH₂Cl₂ / 20 °C

5: 73 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

With Grubbs catalyst first generation; 18-crown-6 ether; montmorillonite K-10; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1: modified Brown allylation / 2: transketalization / 3: Cyclization / 4: Alkylation / 5: Alkylation;
DOI:10.1016/S0040-4039(99)02021-3