PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• CAS No.: 197574-94-0
• Molecular Formula: C16H23 N O6
• Molecular Weight: 325.362
• Mol file: 197574-94-0.mol

Synonyms:PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;Phenylethyl2-acetamido-2-deoxy-b-D-glucopyranoside;PHENYLETHYL 2-ACETAMIDO-2-DEOXY-SS-D-GLUCOPYRANOSIDE

Chemical Property of PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

Chemical Property:

• PSA: 108.25000
• LogP: -0.41970

Purity/Quality:

98%,99%, ^*data from raw suppliers

PHENYLETHYL-2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE

There total 3 articles about PHENYLETHYL 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE 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: 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:

2-phenylethanol (60-12-8) → phenethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (197574-94-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / HgI₂, 3 Angstroem molecular sieves / CH₂Cl₂

2: 90 percent / CH₃ONa / methanol

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

DOI:10.1007/BF02273926

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester (3068-34-6) → phenethyl 2-acetamido-2-deoxy-β-D-glucopyranoside (197574-94-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / HgI₂, 3 Angstroem molecular sieves / CH₂Cl₂

2: 90 percent / CH₃ONa / methanol

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

DOI:10.1007/BF02273926

upstream raw materials:

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

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:

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

Refernces

• 1、 Zemlyakov,Kur'yanov,Tsikalov,Aksenova,Chirva. "Synthesis of hydrophobic derivatives of muramyldipeptides". . p. 61 - 66. Retrieved 2007/10/03.