[(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate
• CAS No.: 197574-92-8
• Molecular Formula: C22H29 N O9
• Molecular Weight: 451.474
• DSSTox Substance ID: DTXSID60429470
• Wikidata: Q82242510
• Mol file: 197574-92-8.mol

Synonyms:[(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate;[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-(2,5-dimethylphenoxy)oxan-2-yl]methyl acetate;DTXSID60429470;HLGSHDLKGYMREZ-ZGJYDULXSA-N;AKOS002688242;3-(acetylamino)-5-(acetyloxy)-6-[(acetyloxy)methyl]-2-(2,5-dimethylphenoxy)tetrahydro-2H-pyran-4-yl acetate;AF-399/41692660;Z1801318715

Chemical Property of [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate

Chemical Property:

• PSA: 126.46000
• LogP: 1.29270
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 451.18423150
• Heavy Atom Count: 32
• Complexity: 697

Purity/Quality:

99%, ^*data from raw suppliers

Phenylethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)C)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C
• Isomeric SMILES: CC1=CC(=C(C=C1)C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C

Technology Process of [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate

There total 1 articles about [(2R,3S,4R,5R,6S)-3,4-bis(acetyloxy)-6-(2,5-dimethylphenoxy)-5-acetamidooxan-2-yl]methyl acetate 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: 57.0%

2-phenylethanol (60-12-8) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenethyloxy-tetrahydro-pyran-4-yl ester (197574-92-8)

Guidance literature:

With 3 A molecular sieve; mercury(II) iodide; In dichloromethane;

DOI:10.1007/BF02273926

Reference yield: 95.0%

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenethyloxy-tetrahydro-pyran-4-yl ester (197574-92-8) → phenethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (197574-94-0)

Guidance literature:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenethyloxy-tetrahydro-pyran-4-yl ester; With sodium methylate; In methanol; at 20 ℃; for 2h;

In methanol; at 20 ℃; pH=7;

DOI:10.1016/j.bmc.2011.07.031

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenethyloxy-tetrahydro-pyran-4-yl ester (197574-92-8) → N-((4aR,6R,7R,8R,8aS)-8-Hydroxy-6-phenethyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide (197574-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CH₃ONa / methanol

2: 87 percent / H₂SO₄ / dioxane; methanol / 0.08 h / 90 - 95 °C

With sulfuric acid; sodium methylate; In 1,4-dioxane; methanol;

DOI:10.1007/BF02273926

upstream raw materials:

2-phenylethanol

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Downstream raw materials:

phenethyl 2-acetamido-2-deoxy-β-D-glucopyranoside

N-((4aR,6R,7R,8R,8aS)-8-Hydroxy-6-phenethyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide

(R)-2-((4aR,6R,7R,8R,8aS)-7-Acetylamino-6-phenethyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-propionic acid

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