55697-50-2

Upstream product

• 129165-07-7 methyl 3-O-allyl-2,4,6-tri-O-benzyl-alpha-D-galactopyranoside 
• 53685-11-3 (2R,3R,4S,5R,6S)-5-Benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol 
• 100-44-7 benzyl chloride 
• 88825-12-1 (2S,3R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3,4-diol 
• 139710-12-6 Methyl 2,4,6-tri-O-benzyl-3-crotyl-α-D-galactopyranoside 
• 620-05-3 iodomethylbenzene 
• 100-39-0 benzyl bromide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 160533-90-4 methyl 2,4,6-tri-O-benzyl-3-O-(methylthio)thiocarbonyl-α-D-galactopyranoside 
• 260411-23-2 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-4-(naphthalen-2-ylmethoxy)-tetrahydro-pyran 
• 260411-21-0 methyl 3-O-NAP-α-D-galactoside 
• 129165-06-6 methyl 3-O-allyl-α-D-galactopyranoside 
• 139710-11-5 Methyl 3-O-crotyl-α-D-galactopyranoside 
• 81928-95-2 (2S,3R,4S,5S,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran 

Downstream Products

• 139710-14-8 Methyl 2,4,6-tri-O-benzyl-3-O-(2,3,4-tri-O-acetyl-6-tosyl-α-D-galactopyranosyl)-α-D-galactopyranoside 
• 142698-89-3 methyl 2,4,6-tri-O-benzyl-α-D-xylo-hexopyranosid-3-ulose 
• 129437-64-5 methyl O-(3,4,6-tri-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 160529-95-3 methyl 2,4,6-tri-O-benzyl-α-D-gulopyranoside 
• 139710-10-4 Methyl 3-O-(3,6-anhydro-β-D-galactopyranosyl)-α-D-galactopyranoside 
• 139710-15-9 Methyl 3-O-(3,6-anhydro-β-D-galactopyranosyl)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 129452-02-4 methyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 129165-09-9 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-galactopyranose 
• 129165-08-8 2,4,6-tri-O-benzyl-α-D-galactopyranosyl chloride 
• 120424-73-9 3-O-acetyl-2,4,6-tri-O-benzyl-α-D-galactopyranosyl chloride 
• 160533-90-4 methyl 2,4,6-tri-O-benzyl-3-O-(methylthio)thiocarbonyl-α-D-galactopyranoside 

Relevant academic research and scientific papers

NOVEL GALACTOSIDE INHIBITOR OF GALECTINS

The present invention relates to a D-galactopyranose compound of formula (1) wherein the pyranose ring is α-D-galactopyranose, and these compounds are high affinity galectin-3 inhibitors for use in treatment of inflammation; Inflammation induced thrombosis; Atopic dermatitis; Acute coronary syndrome; fibrosis, such as pulmonary fibrosis, liver fibrosis, kidney fibrosis, ophthalmological fibrosis and fibrosis of the skin and heart; local fibrosis such as Dupuytren's disease and Peyronie's disease; fibrotic complications of other therapies such as coronary stents, bile duct stents, cerebral artery stents, ureter stents; scleroderma; scarring; keloid formation; covid-19; acute lung injury; ARDS; viral pneumonitis, aberrant scar formation; surgical adhesions; septic shock; cancer, such as colorectal cancer, other gastrointestinal carcinomas such as pancreatic cancer, gastric cancer, biliary tract cancer, lung cancers, mesothelioma, female cancers like breast cancer, ovarian cancer, uterine cancer, cancer of the cervix uteri, cancer of the salpingx, cerebral cancers such as medulloblastomao, glioma, meningioma, sarcomas of the bones and muscles and other sarcomas, leukemias and lymphomas, such as T-cell lymphomas; transplant rejection; metastasising cancers; ageing; Dementia; Alzheimers; TGFbeta driven bone disease such as osteogenesis imperfecta; Pulmonary hypertension; autoimmune diseases, such as psoriasis, rheumatoid arthritis, Rheumatoid lung; Crohn's disease, ulcerative colitis, ankylosing spondylitis, systemic lupus erythematosus; viral infections such as influenza virus, HIV, Herpes virus, Coronaviruses, Hepatitis C; metabolic disorders; heart disease; heart failure; pathological angiogenesis, such as ocular angiogenesis or a disease or condition associated with ocular angiogenesis, e.g. neovascularization related to cancer; and eye diseases, such as age-related macular degeneration and corneal neovascularization; atherosclerosis; metabolic diseases; diabetes; type I diabetes; type 2 diabetes; insulin resistens; obesity; Marfans syndrome; Loeys–Dietz syndrome; nephropathy; Diastolic HF; fibrotic lung complications of aPD1 and other CPI therapies; asthma and other interstitial lung diseases, including Hermansky-Pudlak syndrome, liver disorders, such as non- alcoholic steatohepatitis or non-alcoholic fatty liver disease; uterine disease such as uterine fibroids and uterine or cervical fibrosis.

Use of 1,2-dichloro 4,5-dicyanoquinone (DDQ) for cleavage of the 2- naphthylmethyl (NAP) group

The 2-naphthylmethyl (NAP) group is a versatile group for protection of hydroxyl functions. It is stable to 4% TFA in CHCl3, hot 80% HOAc-H2O, SnCl2-AgOTf and HCl-EtOH, but it can readily be removed with DDQ in CH2Cl2.

A simple method for the removal of 4-methoxybenzyl group

Removal of 4-methoxybenzyl group from a series of compounds having various protecting groups has been achieved by treatment with 80% acetic acid in water at 80°C for 4 hours.

Synthesis of some di- and trisaccharides related to the repeating unit of the antigen from Klebsiella type 20

Starting from D-galactose, D-glucuronolactone, and D-mannose, two trisaccharides and two disaccharides related to the repeating unit of Klebsiella type 20 have been synthesised using methyl triflate as promoter with success.

Synthesis of double-chain bis-sulfone neoglycolipids of the 2''-, 3''-, 4''-, and 6''-deoxyglobotrioses

2-(Trimethylsilyl)ethyl (Me3SiCH2CH2) 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-6-O-p-methoxybenzyl-β-D-galactopyranosyl-β-D-glucopyranoside was glycosylated with different 2-, 3-, 4-, or 6-"deoxy-D-galactose" derivatives to give the corresponding deoxytr

Synthesis of methyl O-α-L-rhamnopyranosyl-(12)-α-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue

The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl α-D-galactopyranoside.Deoxygenation was achieved via activation of a protected methyl α

Efficient and stereoselective synthesis of methyl 3-O-(3,6-anhydro-β-D-galactopyranosyl)-α-D-galactopyranoside and methyl 3,6-anhydro-4-O-β-D-galactopyranosyl-α-D-galactopyranoside

Methyl 3-O-(3,6-anhydro-β-D-galactopyranosyl)-α-D-galactopyranoside (3) and methyl 3,6-anhydro-4-O-β-D-galactopyranosyl-α-D-galactopyranoside (4) have been synthesised stereoselectively using three coupling procedures. Acceptable yields were achieved usin

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.

Partial Benzylation of Methyl α- and β-D-Galactopyranosides

Partial benzylation of methyl α-D-galactopyranoside with benzyl chloride and LiOH selectively gave the 2,3,6-tribenzyl ether, while that using KOH or RbOH gave the 2,4,6-isomer as the main product.Methyl β-D-galactopyranoside afforded the 3,4,6-tribenzyl ether predominantly, irrespective of the alkali used.