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
• Article Data: 5

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

Downstream Products

• 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 
• 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 
• 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 
• 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 
• 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 
• 82659-55-0 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 
• 117238-41-2 Acetic acid (2S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylmethyl)-tetrahydro-pyran-2-yl ester 
• 145064-86-4 Methyl O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 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 

Relevant articles and documents

Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase

Separation of the diastereomers of glycosyl sulfoxides differing in the sulfur chirality has been difficult. This article presents a fast and scalable method for their diastereoseparation using a chiral stationary phase. The usefulness of this method was

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

Treatment of glycopyranosyl phenyl sulfoxides 2ah, l, 2bh, l with two equivalents of lithium diisopropylamide provides directly the C-2-lithiated glycal intermediates 3aAh, l, 3bAh, l which, on reaction with formaldehyde as electrophile, furnish the 2-hyd