3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Base Information

Chemical Name:3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose
CAS No.:799280-88-9
Molecular Formula:C₂₀H₂₆O₅
Molecular Weight:346.423
Hs Code.:

Synonyms:3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

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Chemical Property of 3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

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Technology Process of 3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

There total 7 articles about 3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose 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: 83.0%

: 799281-04-2
Methanesulfonic acid (R)-1-[(3aR,5R,6R,6aR)-6-((R)-1-benzyloxymethyl-allyl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-methanesulfonyloxy-ethyl ester

: 799280-88-9
3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: With sodium iodide; In butanone; for 4h; Heating;
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

: 799280-88-9
3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 100-39-0
benzyl bromide

: 799280-88-9
3-C-[(R)-1-benzyloxymethyl-prop-2-enyl]-5,6-dideoxy-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: Multi-step reaction with 4 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

With sulfuric acid; N-ethyl-N,N-diisopropylamine; sodium iodide; silver(l) oxide; In methanol; dichloromethane; butanone;
DOI:10.1016/j.tet.2004.08.092