(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane
CAS No.:1453285-72-7
Molecular Formula:C₂₄H₃₀O₅
Molecular Weight:398.499
Hs Code.:

Synonyms:(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

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Technology Process of (R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

There total 6 articles about (R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-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: 94.0%

: 1453285-71-6
((2R,3R)-3-((S)-2-(benzyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)oxiran-2-yl)methanol

: 100-39-0
benzyl bromide

: 1453285-72-7
(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 12h;
DOI:10.1016/j.tet.2013.07.072

Reference yield:

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 1453285-72-7
(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 - 20 °C / Inert atmosphere

2.1: ozone / dichloromethane / -78 °C

2.2: 2 h / 0 °C

3.1: benzene / 2 h / 20 °C

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C

5.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

5.2: 12 h / -20 °C / Molecular sieve

6.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; ozone; In tetrahydrofuran; dichloromethane; toluene; mineral oil; benzene; 3.1: |Wittig Olefination / 5.1: |Sharpless Asymmetric Epoxidation / 5.2: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tet.2013.07.072

Reference yield:

: 1453285-70-5
(S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

: 1453285-72-7
(R)-4-((S)-1-(benzyloxy)-2-((2R,3R)-3-((benzyloxy)methyl)oxiran-2-yl)ethyl)-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

1.2: 12 h / -20 °C / Molecular sieve

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; tetra-(n-butyl)ammonium iodide; sodium hydride; D-(-)-diisopropyl tartrate; In tetrahydrofuran; dichloromethane; mineral oil; 1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tet.2013.07.072