2-Naphthyl beta-D-glucopyranoside

Base Information

• Chemical Name: 2-Naphthyl beta-D-glucopyranoside
• CAS No.: 6044-30-0
• Molecular Formula: C16H18O6
• Molecular Weight: 306.315
• Hs Code.: 2932999099
• European Community (EC) Number: 227-933-8
• DSSTox Substance ID: DTXSID50874798
• Nikkaji Number: J227.251B
• Wikidata: Q27162434
• ChEMBL ID: CHEMBL4469508
• Mol file: 6044-30-0.mol

Synonyms:6044-30-0;2-Naphthyl beta-D-glucopyranoside;2-Naphthyl b-D-glucopyranoside;2-NAPHTHYL-BETA-D-GLUCOPYRANOSIDE;2-naphthyl beta-D-glucoside;EINECS 227-933-8;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(naphthalen-2-yloxy)tetrahydro-2H-pyran-3,4,5-triol;2-naphthol glucoside;beta-naphthol glucoside;ChemDiv1_023898;2-Naphthylb-D-glucopyranoside;SCHEMBL8104495;CHEMBL4469508;CHEBI:90258;HMS654O06;DTXSID50874798;AMY41376;b-D-Glucopyranoside, 2-naphthalenyl;MFCD00067623;2-Naphthalenyl beta-D-glucopyranoside;AKOS001660076;DS-5085;naphthalen-2-yl beta-D-glucopyranoside;CS-0322827;2-Naphthyl I(2)-D-glucopyranoside monohydrate;C75823;A868977;SR-01000463452;SR-01000463452-1;Q27162434;(2R,3S,4S,5R,6S)-2-(HYDROXYMETHYL)-6-(NAPHTHALEN-2-YLOXY)OXANE-3,4,5-TRIOL

Chemical Property of 2-Naphthyl beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 9.25E-16mmHg at 25°C
• Melting Point: 183 °C
• Refractive Index: 1.654
• Boiling Point: 567.9 °C at 760 mmHg
• PKA: 12.80±0.70(Predicted)
• Flash Point: 297.3 °C
• PSA: 99.38000
• Density: 1.454 g/cm³
• LogP: 0.01850
• Storage Temp.: 2-8°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 306.11033829
• Heavy Atom Count: 22
• Complexity: 365

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C1=CC=C2C=C(C=CC2=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

Technology Process of 2-Naphthyl beta-D-glucopyranoside

There total 12 articles about 2-Naphthyl 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: 99.0%

1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (37812-69-4) → naphthyl-beta-D-glucopyranoside (6044-30-0)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/j.tet.2020.130965

Reference yield: 89.0%

UDP-glucose (133-89-1) + β-naphthol (135-19-3) → naphthyl-beta-D-glucopyranoside (6044-30-0)

Guidance literature:

With Aloe*arborescens*glycosyltransferase*GT₃; In dimethyl sulfoxide; at 30 ℃; for 12h; pH=7.4; Enzymatic reaction;

DOI:10.1016/j.tetlet.2017.04.041

Reference yield:

2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6) → naphthyl-beta-D-glucopyranoside (6044-30-0)

Guidance literature:

With methanol; ammonia;

DOI:10.1039/jr9300002729

upstream raw materials:

2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

D-glucose pentaacetate

β-naphthol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2-Naphthol glucuronide

D-Glucose

β-naphthol

2-naphthyl 4,6-O-benzylidene-2,3-di-O-acetyl-β-D-glucopyranoside

Refernces

• 1、 Xie, Kebo,Zhang, Yujiao,Chen, Ridao,Chen, Dawei,Yang, Lin,Liu, Xia,Dai, Jungui. "Enzymatic glucosylation of unnatural naphthols by a promiscuous glycosyltransferase from Aloe arborescens". supporting information. p. 2118 - 2121. Retrieved 2017/05/09.
• 2、 Smits,Engberts,Kelogg,Van Doren. "Non-amphiphilic carbohydrate liquid crystals containing an intact monosaccharide moiety". . p. 185 - 199. Retrieved 2007/10/02.