(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Base Information

Chemical Name:(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene
CAS No.:817201-08-4
Molecular Formula:C₁₂H₂₀O₄
Molecular Weight:228.288
Hs Code.:

Synonyms:(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

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Chemical Property of (1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

There total 1 articles about (1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene 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:

: 6118-51-0
exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

: 817201-08-4
(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran / 20 h / 0 °C

2: 2.92 g / pyridine / 17 h / 20 °C

3: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

4: 97 percent / PPTS / CH₂Cl₂ / 1 h / 20 °C

5: 100 percent / NaOMe / methanol / 2 h / 20 °C

With pyridine; lithium aluminium tetrahydride; Lipase PS (Amano); water; sodium methylate; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo048566j

Reference yield:

: 817201-08-4
(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

: 58479-61-1
tert-butylchlorodiphenylsilane

: 817201-09-5
(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 23h;
DOI:10.1021/jo048566j

Reference yield:

: 817201-08-4
(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

: 817201-14-2
(2R,3S,4S,5S)-3-(tert-butyldiphenylsilyloxy)methyl-2,5-bis(hydroxymethyl)-4-methyltetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 23 h / 0 °C

2: 3.82 g / aq. AcOH / tetrahydrofuran / 5 h / 20 °C

3: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C

4: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C

5: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

6: Pb(OAc)4 / benzene / 0.75 h / 20 °C

7: 2.04 g / NaBH₄ / methanol / 1 h / 20 °C

With 1H-imidazole; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; water; tri-n-butyl-tin hydride; sodium hydride; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1021/jo048566j