25878-57-3

Basic information

• Product Name: 1,6-anhydrolactose hexaacetate
• Synonyms: 1,6-anhydrolactose hexaacetate;Lactosan hexaacetate
• CAS NO: 25878-57-3
• Molecular Formula: C₂₄H₃₂O₁₆
• Molecular Weight: 576.50128
• Mol File: 25878-57-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 598°Cat760mmHg
• Flash Point: 252°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 2.92E-14mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: 1,6-anhydrolactose hexaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-anhydrolactose hexaacetate(25878-57-3)
• EPA Substance Registry System: 1,6-anhydrolactose hexaacetate(25878-57-3)

Safety Data

• Hazardous Substances Data: 25878-57-3(Hazardous Substances Data)

Usage

Chemical compound

A substance formed by the reaction of lactose with acetic anhydride, resulting in the removal of a water molecule and the addition of six acetyl groups.

Derived from lactose

Lactose is a naturally occurring sugar found in milk.

Pharmaceutical industry use

1,6-anhydrolactose hexaacetate is commonly used as a prodrug, which means it is converted into an active drug after being metabolized in the body.

Potential as a carrier for delivering drugs to the brain

1,6-anhydrolactose hexaacetate has been studied for its ability to cross the blood-brain barrier and deliver drugs to the brain.

Ability to promote bone health and healing

1,6-anhydrolactose hexaacetate has shown potential for promoting bone health and healing, although further research is needed to fully understand its therapeutic applications.

Potential treatment for diabetes and liver disease

1,6-anhydrolactose hexaacetate has shown potential as a treatment for diabetes and liver disease, although further research is needed to fully understand its therapeutic applications.

Further research needed

More research is needed to fully understand the potential therapeutic applications of 1,6-anhydrolactose hexaacetate.

InChI:InChI=1/C24H32O16/c1-9(25)31-17-15-7-8-16(36-15)18(19(17)32-10(2)26)37-23-21(34-12(4)28)20(33-11(3)27)22(35-13(5)29)24(38-23)40-39-14(6)30/h15-24H,7-8H2,1-6H3/t15-,16+,17+,18-,19-,20-,21-,22-,23-,24-/m1/s1

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 14690-00-7 2-O-benzylglycerol 
• 141243-55-2 1,2,3,2',3',4',6'-Hepta-O-acetyl-6-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)-β-lactose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 5346-69-0 O²,O³-isopropylidene-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose 
• 108-24-7 acetic anhydride 
• 7225-54-9 O⁴-(Tetra-O-acetyl-β-D-glucopyranosyl)-1,6-anhydro-β-D-mannopyranose 

Downstream Products

• 138-22-7 n-butyl lactate 
• 5505-63-5 D-mannosamine hydrochloride 
• 1624603-21-9 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-3-chloro-1,7-naphthyridin-8-amine 
• 1600506-73-7 N-(3-((3R)-5-amino-3,6,6-trimethyl-1,1-dioxido-3,6-dihydro-2H-1,4-thiazin-3-yl)-4-fluorophenyl)-3-methoxy-1,7-naphthyridin-8-amine 
• 1600511-18-9 N-(3-((3R)-5-amino-3,6,6-trimethyl-1,1-dioxido-3,6-dihydro-2H-1,4-thiazin-3-yl)-4-fluorophenyl)-3-bromopyrido[2,3-d]pyridazin-8-amine 
• 73139-43-2 4-O-(6-O-triphenylmethyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-β-D-glucopyranose 
• 73139-45-4 O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose 
• 108202-94-4 6'-O-acetyl-1,6-anhydro-2,2',3,3',4'-penta-O-benzyl-β-D-lactose 
• 90318-51-7 1,6-Anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-O-trityl-β-D-galactopyranosyl)-β-D-glucopyranose 
• 141243-54-1 benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3-di-O-acetyl-β-D-glucopyranoside 
• 141243-56-3 3,6,2',3',4',6'-Hexa-O-acetyl-1,2-O-(2,3,2',3',4',6'-hexa-O-acetyl-1-O-benzyl-β-lactos-6-yl orthoacetyl)-α-lactose 
• 86461-98-5 O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose 
• 34395-01-2 O-β-D-galactopyranosyl-(1<*>4)-1,6-anhydro-β-D-glucopyranoside 

Relevant articles and documents

Synthesis and characterization of 6-O-β-lactosyl-α,β-lactoses, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols, and 4,6-di-O-β-D-galactopyranosyl-α,β-D-glucoses

1,2,3,2',3',4',6'-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2',3',4',6'-hepta-O-acetyl-α-lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2',3',4',6'-hepta-O-acetyl-6-O-(2,3,6,2',3',4',6'-hepta-O- acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2',3',4',6'-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(2,3,2',3',4',6'-hexa-O-acetyl-1- O-benzyl-β-lactos-6-yl orthoacetyl)-α-lactose (63%) and 3,6,2',3',4',6'-hexa-O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D-galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions 11 reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl-1-O-{2',3',4',6'-hexa-O-acetyl-6-O-(2,3,6,2',3' ,4',6'-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-(R,S)-glycerols (16%). 1,2,3,2′,3′,4′,6′-Hepta-O-acetyl-β-lactose (4) was coupled with 2,3,6,2′,3′,4′,6′-hepta-O-Acetyl-α- lactosyl bromide (7) in the presence of Hg(CN)2 to afford 1,2,3,2′,3′,4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3$ PRM, 4′,6′-hepta-O-acetyl-6-O-(2,3,6,2′,3′, 4′,-hepta-O-acetyl-β-lactosyl)-β-lactose (11) which, upon O-deacetylation, gave 6-O-β-lactosyl-α,β-lactoses (64% from 4). In contrast, the reaction of 7 with benzyl 2,3,2′,3′,4′,6′-hexa-O-acetyl-β-lactoside in the presence of Hg(CN)2 produced 3,6,2′,3′,4′,6′-hexa-O- acetyl-1,2-O-(2,3,2′,3′,4′,6′-hexa-O-acetyl-1-O-benzy l- β-lactos-6-yl orthoacctyl)-α-lactose (63%) and 3,6,2′,3′,4′,6′-hexa- O-acetyl-1,2-O-(1-cyanoethylidene)-α-lactose (27%). The glycosidation of 4 using 2,3,4,6-tetra-O-acetyl-α-D- galactoyranosyl bromide in the presence of Hg(CN)2 afforded, after deprotection, 4,6-di-O-β-D- galactopyranosyl-α,β-D-glucoses (66%). The reaction of 11 with 1,2-di-O-benzyl-(R,S)-glycerols and trimethylsilyl trifluoromethanesulfonate yielded, after deprotection, 1-O-(6-O-β-lactosyl-β-lactosyl)-(R,S)-glycerols (18%). Under the same coupling conditions II reacted with 2-O-benzylglycerol to form 3-O-acetyl-2-O-benzyl- O-{2′,3′,4′,6′-hexa-O-acetyl-6-O-(2,3,6,2′,3 ′, 4′,6′-hepta-O-acetyl-β-lactosyl)-β-lactosyl}-( R,S)- glycerols (16%).