(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Base Information

Chemical Name:(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol
CAS No.:808737-09-9
Molecular Formula:C₂₀H₂₇IO₁₀
Molecular Weight:554.333
Hs Code.:

(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Synonyms:(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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Chemical Property of (2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

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Technology Process of (2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

There total 1 articles about (2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-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:

: (2R,4aR,6R,7R,8R,8aS)-6-((2R,3S,4R,5R)-4,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 808737-09-9
(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In toluene; at 90 ℃; for 3h;
DOI:10.1016/j.carres.2004.07.022

Reference yield: 92.0%

: 108-24-7
acetic anhydride

: 808737-09-9
(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 801287-87-6
methyl 2,2',3,3'-tetra-O-acetyl-4',6'-O-benzylidene-6-deoxy-6-iodo-α,β-D-maltoside

Guidance literature:: With dmap; In pyridine; for 15h;
DOI:10.1016/j.carres.2004.07.022

Reference yield:

: 808737-09-9
(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: (2S,3R)-4-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,3,6-trihydroxy-5-oxo-hexanal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / 4-dimethylaminopyridine / pyridine / 15 h

2.1: 80 percent / AgF / pyridine / 21 h / 20 °C

3.1: 78 percent / 3-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂; H₂O / 9 h / 20 °C

4.1: NaOMe / methanol / 24 h / 0 °C

4.2: Amberlite IR 120 (H+) / H₂O / 4 h

With dmap; sodium methylate; silver fluoride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In pyridine; methanol; dichloromethane; water;
DOI:10.1016/j.carres.2004.07.022