2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

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Chemical Name:2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester
CAS No.:343262-60-2
Molecular Formula:C₂₄H₃₆O₆
Molecular Weight:420.546
Hs Code.:

Synonyms:

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Chemical Property of 2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

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Technology Process of 2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

There total 13 articles about 2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl 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:

: 3282-30-2
pivaloyl chloride

: 343262-60-2
2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

2: 82 percent / TBAF / tetrahydrofuran / 24 h / 40 °C

3: 90 percent / CSA / CH₂Cl₂ / 4 h

With pyridine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol015753k

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 343262-60-2
2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 67 percent / CSA / CH₂Cl₂ / 40 h

2: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

3: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

4: 88 percent / CH₂Cl₂ / 1.5 h

5: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH₂Cl₂ / 0.67 h

7: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

8: 82 percent / TBAF / tetrahydrofuran / 24 h / 40 °C

9: 90 percent / CSA / CH₂Cl₂ / 4 h

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; AD-mix-α; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 4: Wittig olefination;
DOI:10.1021/ol015753k

Reference yield:

: 251318-99-7
(S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one

: 343262-60-2
2,2-dimethylpropionic acid 2S-hydroxy-2-(E)-[4S-(4-methoxybenzyloxy)-5R-methyl-6R-propenyltetrahydropyran-2R-yl]ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 99 percent / imidazole / CH₂Cl₂ / 20 h

2: 86 percent / LiBH₄ / diethyl ether; H₂O / -20 - 5 °C

3: 98 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - -30 °C

4: 85 percent / diethyl ether / 3 h / -78 °C

5: 67 percent / CSA / CH₂Cl₂ / 40 h

6: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

7: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

8: 88 percent / CH₂Cl₂ / 1.5 h

9: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

10: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH₂Cl₂ / 0.67 h

11: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

12: 82 percent / TBAF / tetrahydrofuran / 24 h / 40 °C

13: 90 percent / CSA / CH₂Cl₂ / 4 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; AD-mix-α; lithium borohydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; 3: Swern oxidation / 8: Wittig olefination;
DOI:10.1021/ol015753k