3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Base Information

Chemical Name:3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose
CAS No.:130469-40-8
Molecular Formula:C₂₀H₂₆O₇
Molecular Weight:378.422
Hs Code.:

Synonyms:3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

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Chemical Property of 3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

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Technology Process of 3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

There total 1 articles about 3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-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: 95.0%

: 69832-48-0
((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

: 98-88-4
benzoyl chloride

: 130469-40-8
3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Guidance literature:: With pyridine;
DOI:10.1021/jm00105a054

Reference yield:

: 130469-40-8
3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 130495-83-9
3-deoxy-3-<(benzoyloxy)methyl>-1,2-O-isopropylidene-α-D-allofuranose

Guidance literature:: With hydrogenchloride; In methanol; at 55 ℃; for 1h;
DOI:10.1021/jm00105a054

Reference yield:

: 130469-40-8
3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 129399-08-2
(1R,5R,6R)-6-<(benzoyloxy)methyl>-2,8-dioxabicyclo-<3.2.1>octane

Guidance literature:: Multi-step reaction with 8 steps

1: 1.6percent H₂SO₄ / methanol; CHCl₃ / 84 h

2: pyridine / 2 h / Ambient temperature

3: NaI / butan-2-one / 15 h / Heating

4: 1) BH₃*Me₂S, 2) NaHCO₃, 30percent H₂O₂ / 1a) THF, 0-4 deg C, 24 h, b) THF, methanol, 0 deg C, 1 h, 2) THF, methanol, water, up to r. t., 2 h

5: acidic cation-exchange resin (Dowex 50 W₈) / methanol / 5.5 h / Heating

6: acidic cation-exchange resin (Dowex 50 W₈) / toluene / 0.25 h / Heating

7: 88 percent / pyridine / DMAP / 3 h / Ambient temperature

8: 66 percent / Bu₃SnH, azoisobutyronitrile / toluene / 1 h / 75 °C

With pyridine; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; acidic cation-exchange resin (Dowex 50 W₈); sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydrogencarbonate; sodium iodide; dmap; In methanol; chloroform; toluene; butanone;
DOI:10.1021/jo00012a018