b-Naphthyl b-D-Glucopyranoside Tetraacetate

Base Information

• Chemical Name: b-Naphthyl b-D-Glucopyranoside Tetraacetate
• CAS No.: 14581-89-6
• Molecular Formula: C24H26 O10
• Molecular Weight: 474.464
• Mol file: 14581-89-6.mol

Synonyms:Glucopyranoside,2-naphthyl, tetraacetate (7CI); Glucopyranoside, 2-naphthyl, tetraacetate, b-D- (8CI); b-D-Glucopyranoside,2-naphthalenyl, tetraacetate (9CI)

Chemical Property of b-Naphthyl b-D-Glucopyranoside Tetraacetate

Chemical Property:

• Melting Point: 198-199℃ (benzene )
• Refractive Index: 1.568
• PSA: 123.66000
• LogP: 2.30170
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

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

2-Naphthyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: β-Naphthyl β-D-Glucopyranoside Tetraacetate (cas# 14581-89-6) is a compound useful in organic synthesis.

Technology Process of b-Naphthyl b-D-Glucopyranoside Tetraacetate

There total 9 articles about b-Naphthyl b-D-Glucopyranoside Tetraacetate 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: 74.0%

β-naphthol (135-19-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In chloroform; at 20 ℃;

DOI:10.1080/00397919908086444

Reference yield: 69.0%

β-naphthol (135-19-3) + β-D-glucose pentaacetate (604-69-3) → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; for 48h; Ambient temperature;

DOI:10.1080/10587259508038691

Reference yield: 60.0%

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) + 2-(tributylstannyloxy)naphthalene → 2-naphthyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-89-6)

Guidance literature:

With 3 A molecular sieve; In dichloromethane; Ambient temperature;

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

upstream raw materials:

β-naphthol

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

β-D-glucose pentaacetate

2-naphthyl trimethylsilyl ether

Downstream raw materials:

naphthyl-beta-D-glucopyranoside

Refernces

• 1、 Talisman, Ian J.,Kumar, Vineet,Deschamps, Jeffrey R.,Frisch, Mark,Malhotra, Sanjay V.. "Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions". experimental part. p. 2337 - 2341. Retrieved 2011/12/04.
• 2、 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.