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

Base Information

• Chemical Name: 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
• CAS No.: 92117-66-3
• Molecular Formula: C₃₂H₃₉IO₁₈
• Molecular Weight: 838.555
• Mol file: 92117-66-3.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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:

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

Reference yield: 84.0%

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) → 4,4'-bis-(4-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy)biphenyl

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 110 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo2025652

upstream raw materials:

p-Iodophenol

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