160227-12-3

Basic information

• Product Name: 4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside
• Synonyms: 4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside;4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside LacMP per OAc
• CAS NO: 160227-12-3
• Molecular Formula: C₃₃H₄₂O₁₉
• Molecular Weight: 742.68
• Mol File: 160227-12-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 738.9°C at 760 mmHg
• Flash Point: 299.362°C
• Appearance: /
• Density: 1.361g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• CAS DataBase Reference: 4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside(160227-12-3)
• EPA Substance Registry System: 4-Methoxyphenyl 4-O-(2,3,4,6-Tetra-O-acetyl-beta-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside(160227-12-3)

Safety Data

• Hazardous Substances Data: 160227-12-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C33H42O19/c1-15(34)42-13-24-26(44-17(3)36)28(45-18(4)37)31(48-21(7)40)33(51-24)52-27-25(14-43-16(2)35)50-32(49-23-11-9-22(41-8)10-12-23)30(47-20(6)39)29(27)46-19(5)38/h9-12,24-33H,13-14H2,1-8H3/t24-,25-,26-,27+,28-,29-,30-,31-,32+,33-/m0/s1

Upstream product

• 108-24-7 acetic anhydride 
• 3616-19-1 lactose octaacetate 
• 150-76-5 4-methoxy-phenol 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 

Downstream Products

• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 160227-14-5 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-fluoro-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 
• 160179-81-7 4-Oxo-pentanoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 
• 578007-60-0 p-methoxyphenyl 2,3,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 150412-80-9 4-methoxyphenyl (β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 
• 150412-81-0 para-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Lanthanum trifluoromethane-sulfonate-catalyzed facile synthesis of per-O-acetylated sugars and their one-pot conversion to S-aryl and O-alkyl/aryl glycosides

Lanthanum trifluoromethanesulfonate-catalyzed solvent-free per-O-acetylation with stoichiometric acetic anhydride proceeds in high yield (95%-99%) to afford exclusively pyranose products as anomeric mixtures. Subsequent anomeric substitution employing borontrifluoride etherate and thiols or alcohols furnished the corresponding 1,2-trans-linked thioglycosides and O-glycosides, respectively, in good to excellent overall yield (75%-85%). Alternatively, reaction of free sugars in neat alcohol employing the same catalyst at elevated temperature gives the corresponding 1,2-cis-linked O-glycosides (along with 1,2-trans-linked glycosides as minor product) in good yield (73%-80%). Anomeric mixtures of compounds thus produced were characterized as their per-O-acetylated derivatives.

'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

A stereocontrolled synthesis of globotriaosylceramide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting 'armed-disarmed' glycosidation methodology based on glycosyl donors and acceptors carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl(1→4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient.

Cyclo-glycosylation of (1→4)-linked glycohexaoses: Synthesis of cyclolactohexaose

Cyclo-glycosylation of (2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-{(1→4)-(2,3,6-tri-O-benzyl- β-D-glucopyranosyl)-(1→4)-(2,3,6-tri-O-benzyl-α-D- galactopyranosyl)}2-(1→4)-(2,3,6-tri-O-benzyl-α/ β-glucopyranosyl fluoride and subsequent deprotection of the product gave an excellent yield of cyclo-lactohexaose.