5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Base Information

Chemical Name:5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose
CAS No.:86654-49-1
Molecular Formula:C₂₆H₃₂O₆
Molecular Weight:440.536
Hs Code.:

Synonyms:5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

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Chemical Property of 5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

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Technology Process of 5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

There total 11 articles about 5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose 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: 78.0%

: 98039-13-5
6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hexofuranos-5-ulose

: 19493-09-5
Methylenetriphenylphosphorane

: 86654-49-1
5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Guidance literature:: In tetrahydrofuran; dimethyl sulfoxide; for 8h; Ambient temperature;
DOI:10.1039/P19850000019

Reference yield:

: 21665-16-7,37776-66-2
3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methylene-α-D-ribo-hexofuranose

: 86654-49-1
5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: BH₃ / tetrahydrofuran

With borane; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)81823-7

Reference yield:

: 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

: 86654-49-1
5-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-3-C-(4-methoxybenzyloxymethyl)-α-D-ribo-hex-5-enofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: 93.4 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 2 h / Ambient temperature

2: 86.5 percent / 2 percent H₂SO₄ / methanol / 15 h / Ambient temperature

3: 66.8 percent / pyridine / Ambient temperature

4: 94 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

5: 58 percent / NaH, DMSO / tetrahydrofuran / 40 h / Ambient temperature

6: 82 percent / PCC, molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

7: 78 percent / tetrahydrofuran; dimethylsulfoxide / 8 h / Ambient temperature

With 4 A molecular sieve; sulfuric acid; sodium hydride; potassium carbonate; dimethyl sulfoxide; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1039/P19850000019