4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

Base Information

Chemical Name:4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane
CAS No.:926653-20-5
Molecular Formula:C₂₉H₃₆O₆
Molecular Weight:480.601
Hs Code.:

Synonyms:4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of 4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

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Technology Process of 4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

There total 10 articles about 4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane 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: 91.0%

: 926653-36-3
methanesulfonic acid 1-[2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-(2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(4-methoxy-benzyloxy)-hept-3-ynyl ester

: 926653-20-5
4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: methanesulfonic acid 1-[2-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-(2,2-dimethyl-[1,3]dioxolan-4-yl)-7-(4-methoxy-benzyloxy)-hept-3-ynyl ester; With tetrabutyl ammonium fluoride; In tetrahydrofuran;

With potassium carbonate; In methanol;
DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 926653-20-5
4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine; DMAP / CH₂Cl₂

2.1: H₂ / Pd(OH)2/C / ethyl acetate

3.1: TEA / CH₂Cl₂

4.1: K₂CO₃ / methanol; CH₂Cl₂

5.1: 77 percent / Mg; HgCl₂ / diethyl ether / -50 - -20 °C

6.1: 86 percent / NaH; n-Bu₄NI / tetrahydrofuran

7.1: 81 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

8.1: 88 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

9.1: TBAF / tetrahydrofuran

9.2: 91 percent / K₂CO₃ / methanol

With pyridine; dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; magnesium; mercury dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; 7.1: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2006.11.080

Reference yield:

: 94451-14-6
(2S,4'S)-2-Benzyloxy-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-ethyl acetate

: 926653-20-5
4-[6-(3-benzyloxymethyl-oxiranyl)-1-(4-methoxy-benzyloxy)-hex-4-ynyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 8 steps

1.1: H₂ / Pd(OH)2/C / ethyl acetate

2.1: TEA / CH₂Cl₂

3.1: K₂CO₃ / methanol; CH₂Cl₂

4.1: 77 percent / Mg; HgCl₂ / diethyl ether / -50 - -20 °C

5.1: 86 percent / NaH; n-Bu₄NI / tetrahydrofuran

6.1: 81 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

7.1: 88 percent / TEA; DMAP / CH₂Cl₂ / 0 °C

8.1: TBAF / tetrahydrofuran

8.2: 91 percent / K₂CO₃ / methanol

With dmap; n-butyllithium; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; magnesium; mercury dichloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; 6.1: Yamaguchi reaction;
DOI:10.1016/j.tetlet.2006.11.080