Naphthyl-alpha-L-fucoside

Base Information

• Chemical Name: Naphthyl-alpha-L-fucoside
• CAS No.: 63503-05-9
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Hs Code.: 2921490090
• European Community (EC) Number: 264-278-7
• DSSTox Substance ID: DTXSID80212907
• Nikkaji Number: J349.246J
• Wikidata: Q27162428
• Mol file: 63503-05-9.mol

Synonyms:naphthyl-alpha-L-fucoside

Chemical Property of Naphthyl-alpha-L-fucoside

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Melting Point: 196oC ± 3oC
• Boiling Point: 507.4 °C at 760 mmHg
• Flash Point: 260.7 °C
• PSA: 79.15000
• Density: 1.369 g/cm³
• LogP: 1.04610
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 290.11542367
• Heavy Atom Count: 21
• Complexity: 350

Purity/Quality:

98%Min ^*data from raw suppliers

2-Naphthyl-a-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC3=CC=CC=C3C=C2)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)OC2=CC3=CC=CC=C3C=C2)O)O)O

Technology Process of Naphthyl-alpha-L-fucoside

There total 5 articles about Naphthyl-alpha-L-fucoside 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: 89.4%

β-naphthol (135-19-3) + 2,3,4‐tri‐O‐acetyl-α-L‐rhamnopyranosyl chloride (5160-09-8) → 2-naphthyl α-L-rhamnopyranoside (18918-48-4,63503-05-9)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 30 ℃; for 5.5h;

DOI:10.1080/07328303.2017.1390578

Reference yield:

2-naphthyl 2,3,4-triacetyl-α-L-rhamnose (18918-47-3) → 2-naphthyl α-L-rhamnopyranoside (18918-48-4,63503-05-9)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4020(98)01217-4

Reference yield:

L-rhamnose (73-34-7) → 2-naphthyl α-L-rhamnopyranoside (18918-48-4,63503-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Py

2: 7 percent / 3 Angstroem molecular sieves / 1,2-dichloro-ethane / Ambient temperature

3: NaOMe / methanol

With pyridine; 3 A molecular sieve; sodium methylate; In methanol; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(98)01217-4

upstream raw materials:

2-naphthyl 2,3,4-triacetyl-α-L-rhamnose

L-rhamnose

1,2,3,4-tetra-O-acetyl-L-rhamnopyranose

β-naphthol

Refernces

• 1、 Danieli, Bruno,Peri, Francesco,Roda, Gabriella,Carrea, Giacomo,Riva, Sergio. "On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2". . p. 2045 - 2060. Retrieved 2007/10/03.