ALLYL-TETRA-O-ACETYL-BETA-D-

Base Information

• Chemical Name: ALLYL-TETRA-O-ACETYL-BETA-D-
• CAS No.: 10343-15-4
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.372
• Hs Code.: 29400090
• Mol file: 10343-15-4.mol

Synonyms:Glucopyranoside,allyl, tetraacetate (7CI);Glucopyranoside, allyl, tetraacetate, b-D- (8CI);b-D-Glucopyranoside, 2-propenyl,tetraacetate (9CI);Allyl 2,3,4,6-teatra-O-acetyl-b-D-glucopyranoside;Allyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;Allyl-2，3,4,6-tetra-O-acetyl-b-D-glucopyranoside;

Chemical Property of ALLYL-TETRA-O-ACETYL-BETA-D-

Chemical Property:

• Appearance/Colour: White to Yellow Conforms to Requirement
• Melting Point: 87-90 °C(lit.)
• Boiling Point: 438.6 °C at 760 mmHg
• Flash Point: 189.2 °C
• PSA: 123.66000
• Density: 1.24 g/cm³
• LogP: 0.27210
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Allyl 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:

Technology Process of ALLYL-TETRA-O-ACETYL-BETA-D-

There total 36 articles about ALLYL-TETRA-O-ACETYL-BETA-D- 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%

allyl alcohol (107-18-6) + β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4,39698-55-0,54400-76-9,78730-32-2,119111-31-8,119111-32-9)

Guidance literature:

β-D-glucose pentaacetate; With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.166667h; Molecular sieve;

allyl alcohol; In dichloromethane; at 0 - 20 ℃; for 24h; Molecular sieve;

DOI:10.1021/acs.orglett.0c00503

Reference yield: 98.8%

2-propynyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (211688-84-5) → allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-15-4,39698-55-0,78730-32-2,119111-31-8,119111-32-9,54400-76-9)

Guidance literature:

With quinoline; hydrogen; Lindlar's catalyst; In methanol; for 8h; Ambient temperature;

DOI:10.1016/S0008-6215(97)10104-5

Reference yield: 98.0%

allyl alcohol (107-18-6) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4,39698-55-0,54400-76-9,78730-32-2,119111-31-8,119111-32-9)

Guidance literature:

With copper(II) sulfate; mercury dibromide; mercury(II) oxide; In chloroform; at 0 - 20 ℃; for 10h;

DOI:10.1139/v11-069

upstream raw materials:

allyl alcohol

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

D-glucose pentaacetate

β-D-glucose pentaacetate

Downstream raw materials:

allyl β-D-galactopyranoside

2,3,4,5-tetra-O-acetyl-D-glucopyranose

Allyl-6-O-trityl-β-D-galactopyranosid

12-phenoxy-dodec-2-enyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Refernces

• 1、 Wang, Chao,Sanders, Brian,Baker, David C.. "Synthesis of a glycodendrimer incorporating multiple mannosides on a glucoside core". . p. 959 - 963. Retrieved 2011.
• 2、 Yuasa, Yoko,Yuasa, Yoshifumi. "A practical synthesis of 2,3,4,6-Tetra-O-acetyl-1-O-(2-propenyl)-β-D- glucopyranoside using ZnCl2". . p. 405 - 407. Retrieved 2004.
• 3、 Talley et al.. "-". . p. 2037. Retrieved 1945.
• 4、 Holme, Kevin R.,Hall, Laurance D.. "Preparation and characterization of N-chitosan derivatives". . p. 291 - 306. Retrieved 1992.
• 5、 Tronchet,Zsely,Geoffroy. "Spin-labelled glycolipid analogues: D-glucose series". . p. 245 - 258. Retrieved 1995.
• 6、 Mereyala, Hari Babu,Gurrala, Srinivas Reddy. "A highly diastereoselective, practical synthesis of allyl, propargyl 2,3,4,6-tetra-O-acetyl-β-D-gluco, β-D-galactopyranosides and allyl, propargyl heptaacetyl-β-D-lactosides". . p. 351 - 354. Retrieved 1998.
• 7、 Schmidt,Chatterjee,Dobner,Nuhn. "New modified single chained glycolipids. Part 1: Synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer". . p. 139 - 147. Retrieved 2002.
• 8、 Ali, Tammar Hussein,Tajuddin, Hairul Anuar Bin,Hussen, Rusnah Syahila Duali,Heidelberg, Thorsten. "Increased Emulsion Stability for Reverse Y-Shaped Sugar-Based Surfactants". . p. 881 - 886. Retrieved 2015.
• 9、 Nkosana, Noreen K.,Czyzyk, Daniel J.,Siegel, Zarek S.,Cote, Joy M.,Taylor, Erika A.. "Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A". . p. 594 - 600. Retrieved 2018.
• 10、 Ardá, Ana,Blériot, Yves,Bordes, Alexandra,Désiré, Jér?me,Franconetti, Antonio,Guillard, Jer?me,Jiménez-Barbero, Jesús,Ménand, Micka?l,Perrin, Flavie,Poveda, Ana,Sollogoub, Matthieu,Tripier, Rapha?l,Troadec, Thibault. "Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog". supporting information. . Retrieved 2020/03/26.