(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

Base Information

Chemical Name:(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol
CAS No.:1610954-40-9
Molecular Formula:C₁₈H₂₆O₅
Molecular Weight:322.401
Hs Code.:

Synonyms:(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

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Chemical Property of (S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

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Technology Process of (S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

There total 11 articles about (S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol 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: 78.0%

: 1610954-39-6
((2R,3S)-3-((4R,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol

: 1610954-40-9
(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

Guidance literature:: ((2R,3S)-3-((4R,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)oxiran-2-yl)methanol; With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With ethanol; zinc; Reflux;
DOI:10.1016/j.tetlet.2014.04.068

Reference yield:

: 1610954-29-4
(2S,3R)-1-((tert-butyldimethylsilyl)oxy)-2-hydroxy-5-((4-methoxybenzyl)oxy)pentan-3-yl benzoate

: 1610954-40-9
(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: potassium carbonate; methanol / 2 h / 0 - 20 °C

2.1: pyridinium p-toluenesulfonate / dichloromethane / 6 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C

5.1: benzene / Reflux

6.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C

7.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / 12 h / Molecular sieve

8.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 1 h / 0 - 20 °C

8.2: Reflux

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene; 4.1: |Swern Oxidation / 5.1: |Wittig Olefination / 7.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.04.068

Reference yield:

: 1610954-37-4
(E)-ethyl 3-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

: 1610954-40-9
(S)-1-((4S,5R)-5-(2-((4-methoxybenzyl)oxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / dichloromethane / 12 h / Molecular sieve

3.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 1 h / 0 - 20 °C

3.2: Reflux

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; iodine; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.04.068