2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol

Base Information

• Chemical Name: 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol
• CAS No.: 916988-34-6
• Molecular Formula: C₄₀H₄₀O₇
• Molecular Weight: 632.753

Synonyms:2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol

Chemical Property of 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol

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Technology Process of 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol

There total 2 articles about 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol 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: 19.0%

4,6-di-tert-butyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1,3-dihydroxybenzene (916988-28-8) → 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol (916988-34-6)

Guidance literature:

With trifluoroacetic acid; at 20 ℃;

DOI:10.1016/j.carres.2006.08.022

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-14-1) → 2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol (916988-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / MS 4 Angstroem; TMSOTf / CH₂Cl₂ / 4 h / 0 - 20 °C

2: 19 percent / TFA / 20 °C

With trimethylsilyl trifluoromethanesulfonate; MS 4 Angstroem; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.carres.2006.08.022

Reference yield: 64.0%

2-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-benzene-1,3-diol (916988-34-6) → 2-(β-D-glucopyranosyl)-1,3-dihydroxybenzene (82882-11-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃;

DOI:10.1016/j.carres.2006.08.022

upstream raw materials:

4,6-di-tert-butyl-2-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1,3-dihydroxybenzene

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

Downstream raw materials:

2-(β-D-glucopyranosyl)-1,3-dihydroxybenzene

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