150412-81-0

Usage

Uses

Used in Organic Synthesis:
4-Methoxyphenyl 4-O-(2,3,6-Tri-O-benzyl-beta-D-galactopyranosyl)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside serves as a protecting group agent for hydroxyl groups in organic synthesis. Its role is crucial in controlling the reactivity of specific molecular regions, allowing chemists to selectively modify other parts of the molecule without affecting the protected hydroxyl groups.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 4-Methoxyphenyl 4-O-(2,3,6-Tri-O-benzyl-beta-D-galactopyranosyl)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside is utilized as a protecting group for the hydroxyl groups of carbohydrates. This application is essential for the synthesis of complex carbohydrate structures, where the selective protection and deprotection of hydroxyl groups are necessary to achieve the desired product without unwanted side reactions.
Used in Pharmaceutical and Biochemical Research:
4-Methoxyphenyl 4-O-(2,3,6-Tri-O-benzyl-beta-D-galactopyranosyl)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside may also find applications in pharmaceutical and biochemical research, where the protection and subsequent deprotection of hydroxyl groups in carbohydrate-based drug candidates or biomolecules are required. This allows for the precise manipulation of complex carbohydrate structures, facilitating the development of new drugs and bioactive compounds.
Used in Material Science:
Given its structural features, 4-Methoxyphenyl 4-O-(2,3,6-Tri-O-benzyl-beta-D-galactopyranosyl)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside could potentially be explored in material science for the development of new materials with specific properties, such as stimuli-responsive hydrogels or drug delivery systems, leveraging the compound's ability to protect and reveal hydroxyl groups under certain conditions.

InChI:InChI=1/C61H64O12/c1-63-50-32-34-51(35-33-50)70-60-59(69-41-49-30-18-7-19-31-49)57(67-39-47-26-14-5-15-27-47)55(53(72-60)43-65-37-45-22-10-3-11-23-45)73-61-58(68-40-48-28-16-6-17-29-48)56(66-38-46-24-12-4-13-25-46)54(62)52(71-61)42-64-36-44-20-8-2-9-21-44/h2-35,52-62H,36-43H2,1H3/t52-,53-,54-,55+,56-,57-,58-,59-,60+,61-/m0/s1

Upstream product

• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 150-76-5 4-methoxy-phenol 
• 100-39-0 benzyl bromide 
• 160227-12-3 4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 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 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of the oligosaccharide moiety of the tumor-associated antigen disialosyl globopentaosylceramide

Disialosyl globopentaosylceramide (DSGb5) is often expressed by renal cell carcinomas. To investigate properties of DSGb5, we have prepared its oligosaccharide moiety by chemically synthesizing Gb5 which was enzymatically sialylated using the mammalian sialyltransferases ST3Gal1 and ST6GalNAc5. Glycan microarray binding studies indicate that Siglec-7 does not recognize DSGb5, and preferentially binds Neu5Acα(2,8)Neu5Ac containing glycans.

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.