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

Base Information

Chemical Name:((2R,3R)-3-((S)-2-(benzyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)oxiran-2-yl)methanol
CAS No.:1453285-71-6
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

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

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

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

There total 5 articles about ((2R,3R)-3-((S)-2-(benzyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)oxiran-2-yl)methanol 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: 88.0%

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

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

Guidance literature:: (S,E)-5-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol; With titanium(IV) isopropylate; D-(-)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 0.5h; Molecular sieve;

With tert.-butylhydroperoxide; In dichloromethane; at -20 ℃; for 12h; Molecular sieve;
DOI:10.1016/j.tet.2013.07.072

Reference yield:

: 87604-53-3
(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / dichloromethane / -78 °C

1.2: 2 h / 0 °C

2.1: benzene / 2 h / 20 °C

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

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

4.2: 12 h / -20 °C / Molecular sieve

With titanium(IV) isopropylate; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; ozone; In dichloromethane; toluene; benzene; 2.1: |Wittig Olefination / 4.1: |Sharpless Asymmetric Epoxidation / 4.2: |Sharpless Asymmetric Epoxidation;
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

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

Guidance literature:: Multi-step reaction with 5 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

With titanium(IV) isopropylate; 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