138857-53-1

Basic information

• Product Name: Phenyl 1-thio-beta-D-galactopyranoside 2,3-dibenzoate
• Synonyms: Phenyl 1-thio-beta-D-galactopyranoside 2,3-dibenzoate
• CAS NO: 138857-53-1
• Molecular Weight: 480.538
• Mol File: 138857-53-1.mol

Chemical Properties

• CAS DataBase Reference: Phenyl 1-thio-beta-D-galactopyranoside 2,3-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 1-thio-beta-D-galactopyranoside 2,3-dibenzoate(138857-53-1)
• EPA Substance Registry System: Phenyl 1-thio-beta-D-galactopyranoside 2,3-dibenzoate(138857-53-1)

Safety Data

• Hazardous Substances Data: 138857-53-1(Hazardous Substances Data)

Upstream product

• 138857-52-0 phenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 208644-75-1 phenyl 2,3-di-O-benzoyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 144830-21-7 phenyl 2,3-di-O-benzyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 98-88-4 benzoyl chloride 
• 4163-60-4 β-D-galactose peracetate 
• 167612-33-1 (2R,6S,7R,8R,8aR)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 
• 138922-03-9 phenyl 4,6-O-benzylidene-1-thio-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 

Downstream Products

• 945626-51-7 phenyl 2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside 
• 1290105-19-9 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,3-bis-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilanediyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 
• 1290105-20-2 phenyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-di-tert-butylsilanediyl-α-D-galactopyranosyl)-1-thio-β-D-galactopyranoside 
• 1290105-16-6 C₄₂H₄₂O₇SSi 
• 138857-84-8 (2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzoyloxy-2-methyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester 
• 138857-83-7 phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 
• 154391-12-5 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl fluoride 
• 154391-13-6 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranosyl fluoride 
• 154391-16-9 5-<(benzyloxycarbonyl)amino>pentyl 2,3-di-O-benzoyl-4,6-O<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside 
• 154460-38-5 2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide 
• 208644-74-0 methyl 2,3-di-O-benzoyl-4,6-O-((R)-1-methoxycarbonylethylidene)-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3) 2,4-di-O-benzyl-β-L-fucopyranoside 
• 945626-48-2 1-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-D-galactopyranosyl trichloroacetimidate 
• 945626-52-8 phenyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Synthesis of glycoimmunogen Tn-Thr-PS A1 via hydrazone bond and stability optimization of PS A1 monosaccharide mimics under vaccine development conditions

Previously, our group constructed several immunogens utilizing oxime linkage to conjugate a T-cell stimulatory zwitterionic polysaccharide PS A1 and tumor associated carbohydrate antigens (TACAs) in acetate buffer. Here, a semi-synthetic immunogen was synthesized using hydrazone conjugation between PS A1 and a glycopeptide hydrazide (α-D-GalNAc-L-Thr-NH-NH2) with an excellent loading in PBS buffer. To get robust immune response, the retention of zwitterionic character of PS A1 under vaccine construction conditions is essential. In this regard, the stability of embedded pyruvate acetal moiety in tetrasaccharide repeating unit of PS A1 can validate the retention of the dual charges. Therefore, rather than utilizing this highly immunogenic PS A1 fully, stability studies were performed with synthetic 1-thiophenyl-4,6-O-pyruvate acetal-D-galactopyranose in varying acetate buffer pHs and time intervals. Furthermore, 1-propyl-D-galactofuranose was synthesized to mimick the D-Galf of PS A1 to examine regioselective hydrazone and oxime formation with α-D-GalNAc-L-Thr-NH-NH2 and α-D-GalNAc-ONH2 moieties respectively.

Conformational Distortion Using a Molecular Lever: Synthesis and Conformational Studies of Galactoside Derivatives

Novel bicyclic d-galactose derivatives containing a molecular lever were synthesized and their conformations studied by 1H-NMR and crystallography. Increasing the bulkiness in the alkylidene ring in combination with introducing bulky O-protective groups on the pyranoside ring, causes a ring flip from a 4C1 into the axial rich 1C4 conformation. With less bulky protective groups, the pyranoside ring resides in the 4C1 conformation despite distortion of the external alkylidene ring.

A concise synthesis of globotriaosylsphingosine

Globotriaosylsphingosine (lysoCTH) is produced in the cell by deacylation of the globo-sphingolipid globotriaosylceramide. The latter compound is the major storage material encountered in Fabry patients, an inherited lysosomal storage disorder characteriz

Syntheses of p-nitrophenyl 3- and 4-thio-β-d-glycopyranosides

Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thio

One-pot synthesis of a pentasaccharide with antibiotic activity against Helicobacter pylori

A pentasaccharide that contains the α-1,4-GlcNAc mucin core two-branched O-glycan has been synthesized by a one-pot, two-step glycosylation strategy; this particular carbohydrate motif may provide protection against H. pylori induced pathologies since the

Chemical synthesis of (4,6-Pyr)-Gal β1→4GlcNacβ1→3Fucβ1→OMe: A pyruvated trisaccharide related to the cell aggregation of the sponge Microciona prolifera

4,6-O-[(R)-1-carboxylethylidene] Galβ1→4GlcNAcβ1→3Fucβ1→OMe, a pyruvated trisaccharide unit involved in the aggregation factor of the marine sponge Microciona prolifera, was synthesized stereospecifically and unambiguously employing thioglycosides as glycosyl donors to construct glycosidic bonds.

Lewis Acid-Catalysed Anomerisation and Rearrangement of Alkyl D-Glycopyranosides During Acetalisation with Methyl Pyruvate: How to Utilise it for the Preparation of 1-(Carboxyethylidene)glycopyranosyl Donors

The preparation of 4,6-O-(1-methoxycarbonylethylidene)-D-glycopyranosides 5 starting from 2,3-di-O-benzoyl-D-glycopyranosides 1 and their 4,6-bis-O-trimethylsilyl ethers 2 using methyl 2,2-bis(phenylthio)propionate (4) and methyl pyruvate (3), respectivel