(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

Base Information

Chemical Name:(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate
CAS No.:198768-47-7
Molecular Formula:C₁₃H₁₆O₅
Molecular Weight:252.267
Hs Code.:

Synonyms:(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

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Chemical Property of (-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

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Technology Process of (-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

There total 1 articles about (-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate 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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 154006-52-7
(S)-2,4-dihydroxybutyric acid methyl ester

: 198768-47-7
(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

Guidance literature:: With camphor-10-sulfonic acid; In toluene; for 6h; Yield given; Heating;
DOI:10.1016/S0040-4039(97)10150-2

Reference yield: 86.0%

: 917-54-4
methyllithium

: 198768-47-7
(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

: 198768-49-9
(-)-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]ethanone

Guidance literature:: In tetrahydrofuran; at -100 ℃; for 2h;
DOI:10.1016/S0040-4039(97)10150-2

Reference yield:

: 198768-47-7
(-)-methyl 1-{(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl}-4-carboxylate

: {(2R,3S)-3-[(2S,3E)-2-[(4-methoxybenzyl)oxy]-3-methyl-4-(2-methyl-1,3-thiazol-4-yl)but-3-enyl]-2-methyloxiran-2-yl}methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 86 percent / tetrahydrofuran; diethyl ether / 1.5 h / -100 °C

2.1: NaHMDS / tetrahydrofuran / 0.25 h / -78 °C

2.2: 74 percent / tetrahydrofuran / 1 h / 40 - 50 °C

3.1: DIBALH / CH₂Cl₂; various solvent(s) / 5 h / -20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂; pyridine / 0.25 h / 20 °C

5.1: KHMDS; 18-crown-6 / tetrahydrofuran / 0.42 h / -78 °C

5.2: tetrahydrofuran / 0.5 h / -78 °C

6.1: 98 percent / DIBALH / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

7.1: 83 percent / D-(-)-diisopropyl tartrate; titanium(1V) isopropoxide; tert-butyl hydroperoxide / 4 Angstroem molecular sieves / CH₂Cl₂; various solvent(s) / 72 h / -30 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; sodium hexamethyldisilazane; potassium hexamethylsilazane; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; Dess-Martin periodane; 4 A molecular sieve; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; 2.2: Wittig olefination / 4.1: Swern oxidation / 5.2: Wadsworth-Horner-Emmons olefination / 7.1: Sharpless epoxidation;
DOI:10.1021/jo0007480