(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

Base Information

Chemical Name:(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene
CAS No.:799280-90-3
Molecular Formula:C₂₁H₂₄O₈
Molecular Weight:404.417
Hs Code.:

Synonyms:(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

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Chemical Property of (3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

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Technology Process of (3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

There total 9 articles about (3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-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: 96.0%

: 108-24-7
acetic anhydride

: (3R/S,1R,4R,5R,6R)-6-benzyloxymethyl-3,4,5-trihydroxy-2-oxa-bicyclo[3.3.0]oct-7-ene

: 799280-90-3
(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2004.08.092

Reference yield:

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 799280-90-3
(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

Guidance literature:: Multi-step reaction with 9 steps

1: 52 percent / Zn-Cu couple / diethyl ether / 0.5 h / Heating

2: 83 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C

3: 95 percent / Ag₂O / CH₂Cl₂ / 1 h / 20 °C

4: 80 percent / H₂SO₄ / methanol / 24 h / 20 °C

5: 95 percent / iPr₂NEt / CH₂Cl₂ / 0.08 h / 0 °C

6: 83 percent / NaI / butan-2-one / 4 h / Heating

7: 87 percent / Grubbs' catalyst / benzene / 8 h / Heating

8: 93 percent / aq. AcOH / 2 h / Heating

9: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; lithium aluminium tetrahydride; sulfuric acid; copper; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; zinc; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; butanone; benzene; 1: Reformatsky reaction;
DOI:10.1016/j.tet.2004.08.092

Reference yield:

: 100-39-0
benzyl bromide

: 799280-90-3
(3R/S,1R,4R,5R,6R)-3,4,5-triacetoxy-6-benzyloxymethyl-2-oxa-bicyclo[3.3.0]oct-7-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / Ag₂O / CH₂Cl₂ / 1 h / 20 °C

2: 80 percent / H₂SO₄ / methanol / 24 h / 20 °C

3: 95 percent / iPr₂NEt / CH₂Cl₂ / 0.08 h / 0 °C

4: 83 percent / NaI / butan-2-one / 4 h / Heating

5: 87 percent / Grubbs' catalyst / benzene / 8 h / Heating

6: 93 percent / aq. AcOH / 2 h / Heating

7: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; sulfuric acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; Grubbs catalyst first generation; In methanol; dichloromethane; butanone; benzene;
DOI:10.1016/j.tet.2004.08.092