117307-18-3

Basic information

• Product Name: 2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide
• Synonyms: 2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide
• CAS NO: 117307-18-3
• Molecular Formula: C₄₀H₄₀O₆S
• Molecular Weight: 648.81
• Mol File: 117307-18-3.mol

Chemical Properties

• Boiling Point: 777.6°Cat760mmHg
• Flash Point: 424.1°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 3.63E-23mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide(117307-18-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-benzylgalactopyranosyl phenyl sulfoxide(117307-18-3)

Safety Data

• Hazardous Substances Data: 117307-18-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C40H40O6S/c41-47(35-24-14-5-15-25-35)40-39(45-29-34-22-12-4-13-23-34)38(44-28-33-20-10-3-11-21-33)37(43-27-32-18-8-2-9-19-32)36(46-40)30-42-26-31-16-6-1-7-17-31/h1-25,36-40H,26-30H2/t36-,37+,38+,39-,40+,47?/m1/s1

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 108-98-5 thiophenol 
• 74801-29-9 phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 81307-79-1 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 113421-45-7 Benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->4)-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 145871-25-6 Benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 82659-55-0 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 
• 1380505-22-5 (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 343565-52-6 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 
• 114817-98-0 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran 
• 114817-97-9 (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran 
• 194471-78-8 (2S,3R,4S,5R,6R)-2-methoxy-6-((((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 190515-39-0 (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 41671-29-8 6-O-(tetra-O-benzyl-β-D-galactopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 41671-29-8 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 131684-77-0 (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 
• 125392-60-1 (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 

Relevant articles and documents

Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase

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(Equation Presented) An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford α-allylation products in good to excellent yields, the search for conditions favoring β-selectivity proved less successful.

Synthesis of D-galactopyranosides of trans-4-hydroxy-L-proline utilizing the sulfoxide glycosylation method

Phenyl 1-thio-β-D-galactopyranoside (1) was converted into two sulfoxide glycosyl donors: phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (3) and phenyl (2,3,4,6-tetra-O-pivaloyl)-1-thio-β-D-galactopyranoside S-oxide (5). These glycosyl donors were then each reacted with Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-L-proline allyl ester (7). The glycosylation reactions were conducted at -70°C with triflic anhydride as promotor, in the presence of 2,6-di-tert-butyl-4-methylpyridine. In the case of the perbenzylated sulfoxide donor (3), the major product was Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-benzyl)- α-D-galactopyranosyl]-L-proline allyl ester (8α). In dichloromethane, the α-to-β ratio was 3:1 and in toluene this improved to 5:1, with a combined yield of 41%. In the case of the perpivaloylated sulfoxide donor (5), Nα-fluorenylmethoxycarbonyl-trans-4-hydroxy-4-O-[(2,3,4,6-tetra-O-pivaloyl )-β-D-galactopyranosyl]-L-proline allyl ester (9) was obtained as the sole glycoside product in 46% yield.

Functionally Substituted Vinyl Carbanions, 43. Convenient Transformation of Hexopyranosides into α-Methylene δ-Lactone Derivatives

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