(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol
• CAS No.: 33993-25-8
• Molecular Formula: C16H18O6
• Molecular Weight: 306.315
• Hs Code.: 29389090
• Mol file: 33993-25-8.mol

Synonyms:2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol;2-NAPHTHYL B-D-MANNOPYRANOSIDE;212140-32-4;SCHEMBL14122676;EINECS 251-778-5;2-Naphthalenyl-alpha-D-glucopyranoside;AKOS002346522;beta -Naphthyl alpha -D-Glucopyranoside;FT-0613141;FT-0613146;FT-0772106;(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol

Chemical Property of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol

Chemical Property:

• Appearance/Colour: white to slightly off-white powder
• Melting Point: 196-198 °C
• Boiling Point: 567.9 °C at 760 mmHg
• Flash Point: 297.3 °C
• PSA: 99.38000
• Density: 1.454 g/cm³
• LogP: 0.01850
• Storage Temp.: −20°C
• Solubility.: Ethyl Acetate, Methanol
• 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-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

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

Technology Process of (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol

There total 7 articles about (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-naphthalen-2-yloxyoxane-3,4,5-triol 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: 100.0%

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-2-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate → 2-naphthyl-β-D-galactopyranoside (33993-25-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1021/acs.orglett.8b02925

Reference yield:

C17H27BrNO7PolSi + acetic anhydride (108-24-7) + β-naphthol (135-19-3) → 2-naphthyl-β-D-galactopyranoside (93218-51-0) + 2-naphthyl-β-D-galactopyranoside (33993-25-8)

Guidance literature:

C₁₇H₂₇BrNO₇PolSi; β-naphthol; With dimethylformamide borontrifluoride; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With triethylamine hydrofluoride; In tetrahydrofuran; for 3h; Sealed tube;

acetic anhydride; With pyridine; for 5h; Overall yield = 100 %; Overall yield = 10 mg; stereoselective reaction;

DOI:10.1021/acs.orglett.6b01263

Reference yield:

β-naphthol (135-19-3) + β-D-galactose peracetate (4163-60-4) → 2-naphthyl-β-D-galactopyranoside (33993-25-8)

Guidance literature:

With toluene-4-sulfonic acid; Behandeln mit Ammoniak in Methanol;

DOI:10.1021/ja01132a034

upstream raw materials:

β-naphthol

β-D-galactose peracetate

acetic anhydride

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride

Refernces

• 1、 Kalas, Vasilios,Hibbing, Michael E.,Maddirala, Amarendar Reddy,Chugani, Ryan,Pinkner, Jerome S.,Mydock-McGrane, Laurel K.,Conover, Matt S.,Janetka, James W.,Hultgren, Scott J.. "Structure-based discovery of glycomimetic FmlH ligands as inhibitors of bacterial adhesion during urinary tract infection". . p. E2819 - E2828. Retrieved 2018/03/27.
• 2、 Sinnott,Souchard. "The mechanism of action of beta-galactosidase. Effect of aglycone nature and -deuterium substitution on the hydrolysis of aryl galactosides.". . p. 89 - 98. Retrieved 2007/10/04.