(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 1607459-19-7
• Molecular Formula: C₁₉H₂₀I₂O₉
• Molecular Weight: 646.171

Synonyms:(2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

Chemical Property of (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

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Technology Process of (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

There total 4 articles about (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 80.0%

-benzol (57357-24-1) + D-glucal triacetate (2873-29-2) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (1607459-19-7)

Guidance literature:

With cetyltrimethylammonim bromide; magnesium sulfate; potassium iodide; In dichloromethane; at 0 - 25 ℃; for 6h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo500465m

Reference yield: 74.0%

D-glucal triacetate (2873-29-2) + 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione (61717-82-6) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (1607459-19-7)

Guidance literature:

In chloroform; at 25 ℃; for 0.75h; stereoselective reaction;

DOI:10.1016/j.tet.2017.06.001

Reference yield: 25.0%

Dess-Martin periodane (87413-09-0) + D-glucal triacetate (2873-29-2) → (2R,3R,4S,5S,6R)-2-(acetoxymethyl)-5-iodo-6-((2-iodobenzoyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate (1607459-19-7) + 2-deoxy-2-iodo-1,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (74638-66-7,95672-63-2,113574-79-1,141510-66-9,86964-50-3) + (2R,3S,4S,5R,6R)-6-(acetoxymethyl)-3-iodotetrahydro-2H-pyran-2,4,5-triyl triacetate (113574-79-1)

Guidance literature:

With iodine; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1016/j.tet.2017.06.001

upstream raw materials:

-benzol

D-glucal triacetate

2-Iodobenzoic acid

1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione

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