(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

Base Information

Chemical Name:(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene
CAS No.:380488-79-9
Molecular Formula:C₁₈H₂₂O₅
Molecular Weight:318.37
Hs Code.:

Synonyms:(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

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Chemical Property of (2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

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Technology Process of (2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

There total 6 articles about (2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-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: 80.0%

: 380488-77-7
3-C-allyl-5,6-dideoxy-1,2-O-isopropylidene-3-O-(4-methoxyphenylmethyl)-α-D-ribo-hex-5-enofuranose

: 380488-79-9
(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1021/jo010718c

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 380488-79-9
(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / NaH / tetrahydrofuran / 6 h / 20 °C

2: 75 percent / 0.8percent H₂SO₄ / methanol / 10 h / 20 °C

3: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 64 percent / NaI / butan-2-one / 8 h / Heating

5: 80 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

With dmap; sodium hydride; triethylamine; sodium iodide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; butanone;
DOI:10.1021/jo010718c

Reference yield:

: 175877-45-9
3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 380488-79-9
(2R,3R,4S,5R)-2,3-O-isopropylidene-4-O-(4-methoxyphenylmethyl)-1-oxabicyclo[3.3.0]oct-6-ene

Guidance literature:: Multi-step reaction with 5 steps

1: 86 percent / NaH / tetrahydrofuran / 6 h / 20 °C

2: 75 percent / 0.8percent H₂SO₄ / methanol / 10 h / 20 °C

3: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

4: 64 percent / NaI / butan-2-one / 8 h / Heating

5: 80 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

With dmap; sodium hydride; triethylamine; sodium iodide; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; butanone;
DOI:10.1021/jo010718c