Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

Base Information

Chemical Name:Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester
CAS No.:847910-41-2
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

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Chemical Property of Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

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Technology Process of Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

There total 7 articles about Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl 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: 62.0%

: Acetic acid (S)-1-((2S,3S)-3-formyl-oxiranylmethyl)-3-(4-methoxy-benzyloxy)-propyl ester

: 1779-49-3
Methyltriphenylphosphonium bromide

: 847910-41-2
Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.5h;

Acetic acid (S)-1-((2S,3S)-3-formyl-oxiranylmethyl)-3-(4-methoxy-benzyloxy)-propyl ester; In tetrahydrofuran; at -10 ℃;
DOI:10.1002/anie.200460042

Reference yield:

: Acetic acid (R)-5-hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-pent-3-ynyl ester

: 847910-41-2
Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen; triethylamine / Lindlar's catalyst / tetrahydrofuran / 8 h / 760 Torr

2.1: titanium(IV) isopropylate; DIPT / dichloromethane / 0.5 h / -20 °C

2.2: tert-butyl hydroperoxide / 15; 23 / 16 h / -20 °C

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

4.2: 13 / -10 °C

With titanium(IV) isopropylate; DIPT; hydrogen; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; 1.1: Lindlar hydrogenation / 2.1: Sharpless asymmetric epoxidation / 2.2: Sharpless asymmetric epoxidation / 4.2: Wittig olefination;
DOI:10.1002/anie.200460042

Reference yield:

: 756523-94-1
7-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hept-5-yn-3-ol

: 847910-41-2
Acetic acid (S)-3-(4-methoxy-benzyloxy)-1-((2S,3R)-3-vinyl-oxiranylmethyl)-propyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: pyridine; dmap / dichloromethane / 12 h / 20 °C

2.1: acetic acid / tetrahydrofuran / 2 h / 60 °C

3.1: hydrogen; triethylamine / Lindlar's catalyst / tetrahydrofuran / 8 h / 760 Torr

4.1: titanium(IV) isopropylate; DIPT / dichloromethane / 0.5 h / -20 °C

4.2: tert-butyl hydroperoxide / 15; 23 / 16 h / -20 °C

5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 20 °C

6.2: 13 / -10 °C

With pyridine; titanium(IV) isopropylate; dmap; DIPT; hydrogen; sodium hexamethyldisilazane; Dess-Martin periodane; acetic acid; triethylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; 3.1: Lindlar hydrogenation / 4.1: Sharpless asymmetric epoxidation / 4.2: Sharpless asymmetric epoxidation / 6.2: Wittig olefination;
DOI:10.1002/anie.200460042