159922-68-6

Usage

Uses

Used in Pharmaceutical Industry:
4-METHOXYPHENYL 2,6-DI-O-BENZYL-3,4-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE is used as a key intermediate in the synthesis of sulfated glycosphingolipid SM1a, which is a human epithelial carcinoma antigen. This application is significant because the synthesis of such antigens can contribute to the development of targeted therapies and diagnostic tools for cancer.
The compound's role in the synthesis of biologically relevant molecules highlights its potential utility in the pharmaceutical industry, particularly in the development of novel drugs and therapies for various diseases, including cancer. Its unique structural features make it an attractive candidate for further research and development in the field of medicinal chemistry.

InChI:InChI=1/C30H34O7/c1-30(2)36-26-25(20-32-18-21-10-6-4-7-11-21)35-29(34-24-16-14-23(31-3)15-17-24)28(27(26)37-30)33-19-22-12-8-5-9-13-22/h4-17,25-29H,18-20H2,1-3H3/t25-,26+,27+,28-,29-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 159922-67-5 4-methoxyphenyl 3,4-O-isopropylidene-β-D-galactopyranoside 
• 150-76-5 4-methoxy-phenol 
• 4163-60-4 β-D-galactose peracetate 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 2872-65-3 4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 

Downstream Products

• 1616968-80-9 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranosyl-(1 → 3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 1262589-19-4 p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 1104513-35-0 p-methoxyphenyl 4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 159922-51-7 C₇₉H₈₁NO₁₅S 
• 159922-52-8 (2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-[(2S,3R,4S,5S,6R)-3-benzyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 159922-53-9 C₆₆H₆₉NO₁₄ 
• 159922-54-0 (2S,4S,5R,6R)-5-Acetylamino-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-hydroxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 159922-55-1 C₂₄H₃₃NO₁₄ 
• 635684-69-4 4-methoxyphenyl (methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranuronate)-(1→3)-4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 635684-68-3 4-methoxyphenyl 4-O-benzoyl-2,6-di-O-benzyl-β-D-galactopyranoside 
• 859505-01-4 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 159922-50-6 4-methoxyphenyl 2,6-di-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Total synthesis of sulfated glycosphingolipid SM1a, a kind of human epithelial carcinoma antigen

A highly efficient and practical total synthesis of the sulfated ganglioside SM1a, a kind of human epithelial carcinoma antigen identified in mammalian kidney, has been accomplished for the first time. The characteristic sequence of SM1a, β-D-Galp-(1→3)-β

Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)3 varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry.

Synthesis of some blocked di- and trisaccharide derivatives related to the repeating unit of the O-antigen from Shigella dysenteriae type 3 in the form of their glycosides

Starting from D-galactose and D-galactosamine hydrochloride, two new monosaccharide synthons namely 2-(trimethylsilyl)ethyl 4-O-acetyl-2,6-di-O- benzyl-β-D-galactopyranoside 2 and phenyl 3-O-acetyl-4,6-O-benzylidene-2- deoxy-2-phthalimido-1-thio-β-D-galac

Efficient synthesis of two HNK-1 related pentasaccharides

Two pentasaccharides, representative of those found on complex N-glycans, were synthesized for use as potential substrates for sulfotransferases. The synthesis was achieved by the addition of a disaccharide donor β-D-GlcA(1→3)α-D-Gal-trichloroacetimidate

SYNTHESIS OF HUMAN M BLOOD GROUP ANTIGENIC GLYCOPEPTIDE

A first total synthesis of terminal glycoheptapeptide of human glycophorin AM was accomplished by solution phase peptide condensation utilizing the tetrasaccharide-linked amino acid building blocks designed for Fmoc strategy.