Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 28713-06-6
• Molecular Formula: C₃₂H₃₉IO₁₈
• Molecular Weight: 838.555

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 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: 70.0%

p-Iodophenol (540-38-5) + β-cellobioseoctaacetate (20764-63-0) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (28713-06-6)

Guidance literature:

With iron(III) chloride; In dichloromethane; for 0.666667h; stereoselective reaction; Molecular sieve; Sonication; Inert atmosphere;

DOI:10.1016/j.ultsonch.2014.05.022

Reference yield:

p-Iodophenol (540-38-5) + 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-iodo-phenoxy)-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester (28713-06-6,28713-07-7,92117-66-3,28713-08-8) + C32H39IO18

Guidance literature:

With iron(III) chloride; In dichloromethane; for 0.666667h; Overall yield = 69 %; stereoselective reaction; Molecular sieve; Sonication; Inert atmosphere;

DOI:10.1016/j.ultsonch.2014.05.022

Reference yield: 92.0%

4-iodophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl)-β-D-glucopyranoside (28713-06-6,28713-08-8,92117-66-3,28713-07-7) + trimethylsilylacetylene (1066-54-2) → 4-(trimethylsilylethynyl)phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl)-β-D-glucopyranoside (1261029-40-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1002/cbic.201000447

upstream raw materials:

p-Iodophenol

β-cellobioseoctaacetate

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose

Downstream raw materials:

4-ethynylphenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl)-β-D-glucopyranoside

4-(trimethylsilylethynyl)phenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl)-β-D-glucopyranoside

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