naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

Base Information

• Chemical Name: naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside
• CAS No.: 5335-81-9
• Molecular Formula: C24H26O9S
• Molecular Weight: 490.5228
• Mol file: 5335-81-9.mol

Synonyms:

Chemical Property of naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

Chemical Property:

• Vapor Pressure: 9.62E-14mmHg at 25°C
• Boiling Point: 586.6°Cat760mmHg
• Flash Point: 289.5°C
• Density: 1.33g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside

There total 4 articles about naphthalen-1-yl 2,3,4,6-tetra-O-acetyl-1-thiohexopyranoside 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: 85.0%

tetraacetyl thioglucose (19879-84-6) + 1-Iodonaphthalene (90-14-2) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-1-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (5335-81-9)

Guidance literature:

With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; diisopropylammonium bis(catecholato)isobutylsilicate; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; In N,N-dimethyl-formamide; at 25 ℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;

DOI:10.1021/acs.orglett.9b01730

Reference yield: 77.0%

tetraacetyl thioglucose (19879-84-6) + 1-Bromonaphthalene (90-11-9) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-1-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (5335-81-9)

Guidance literature:

With 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide; nickel dibromide; In N,N-dimethyl-formamide; at 20 ℃; for 3h; Electrochemical reaction; Inert atmosphere;

DOI:10.1039/d0cc01126f

Reference yield:

tetraacetyl thioglucose (19879-84-6) + 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate (780820-43-1) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-2-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (84635-39-2) + (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(naphthalen-1-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (5335-81-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In acetonitrile; at 25 ℃; for 2h; Overall yield = 87 percent; Schlenk technique; Inert atmosphere;

DOI:10.1039/d1ra04013h

upstream raw materials:

1-Naphthalenethiol

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

tetraacetyl thioglucose

1-Iodonaphthalene

Refernces

• 1、 Alami, Mouad,Messaoudi, Samir,Zhu, Mingxiang. "Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides". supporting information. p. 4464 - 4467. Retrieved 2020/05/05.