2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside

Base Information

• Chemical Name: 2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside
• CAS No.: 131531-82-3
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368
• DSSTox Substance ID: DTXSID90425066
• Wikidata: Q82237817
• Mol file: 131531-82-3.mol

Synonyms:131531-82-3;2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside;N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-naphthalen-2-yloxyoxan-3-yl]acetamide;beta-D-Glucopyranoside, 2-naphthalenyl 2-(acetylamino)-2-deoxy-;(2/'-NAPHTHYL) 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDE;ChemDiv1_023850;HMS654M02;SCHEMBL8986150;DTXSID90425066;AKOS002688253;W-201052;Z1801318742

Chemical Property of 2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside

Chemical Property:

• PSA: 108.25000
• LogP: 0.55320
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 347.13688739
• Heavy Atom Count: 25
• Complexity: 461

Purity/Quality:

98%Min ^*data from raw suppliers

2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2=CC3=CC=CC=C3C=C2)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=CC3=CC=CC=C3C=C2)CO)O)O

Technology Process of 2-Naphthyl 2-acetamido-2-deoxy-b-D-glucopyranoside

There total 7 articles about 2-Naphthyl 2-acetamido-2-deoxy-b-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: 99.0%

1-(2-naphthyl) 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside (131531-80-1) → 1-(2-naphthyl) 2-acetamido-2-deoxy-β-D-glucopyranoside (131531-82-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/j.bmc.2004.01.013

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) → 1-(2-naphthyl) 2-acetamido-2-deoxy-β-D-glucopyranoside (131531-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / tetrabutylammonium bromide; aq. NaOH / CH₂Cl₂ / 0.83 h / 20 °C

2: 99 percent / NaOMe / methanol / 1 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2004.01.013

Reference yield:

β-naphthol (135-19-3) → 1-(2-naphthyl) 2-acetamido-2-deoxy-β-D-glucopyranoside (131531-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / tetrabutylammonium bromide; aq. NaOH / CH₂Cl₂ / 0.83 h / 20 °C

2: 99 percent / NaOMe / methanol / 1 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2004.01.013

upstream raw materials:

1-(2-naphthyl) 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside

β-naphthol

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

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

Downstream raw materials:

O-(2-naphthyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester

O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester

Refernces

• 1、 Sasaki, Kenji,Nishida, Yoshihiro,Kambara, Mikie,Uzawa, Hirotaka,Takahashi, Tadanobu,Suzuki, Takashi,Suzuki, Yasuo,Kobayashi, Kazukiyo. "Design of N-acetyl-6-sulfo-β-D-glucosaminide-based inhibitors of influenza virus sialidase". . p. 1367 - 1375. Retrieved 2007/10/03.
• 2、 Chung, Sang J.,Takayama, Shuichi,Wong, Chi-Huey. "Acceptor substrate-based selective inhibition of galactosyltransferases". . p. 3359 - 3364. Retrieved 2007/10/03.