400091-16-9

Basic information

• Product Name: phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside
• Synonyms: phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside
• CAS NO: 400091-16-9
• Molecular Weight: 486.629
• Mol File: 400091-16-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside(400091-16-9)
• EPA Substance Registry System: phenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside(400091-16-9)

Safety Data

• Hazardous Substances Data: 400091-16-9(Hazardous Substances Data)

Upstream product

• 400091-06-7 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-2-O-pivaloyl-β-D-galactopyranoside 
• 3150-20-7 4-methoxyphenyl β-D-galactopyranoside 
• 400091-17-0 phenyl 3-O-allyl-1-thio-β-D-galactopyranoside 
• 400091-05-6 4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 144985-19-3 p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 400091-19-2 phenyl 3-O-allyl-4,6-O-benzylidene-2-O-pivaloyl-1-thio-β-D-galactopyranoside 
• 108-98-5 thiophenol 
• 400091-07-8 4-methoxyphenyl 3-O-allyl-6-O-benzyl-2-O-pivaloyl-β-D-galactopyranoside 
• 400091-03-4 4-methoxyphenyl 3-O-allyl-6-O-benzyl-β-D-galactopyranoside 
• 400091-18-1 phenyl 3-O-allyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 

Downstream Products

• 400091-21-6 phenyl 4-O-acetyl-3-O-allyl-6-O-benzyl-2-O-pivaloyl-1-thio-β-D-galactopyranoside 

Relevant articles and documents

Directed and efficient syntheses of β(1→4)-linked galacto-oligosaccharides

Straightforward, preparatively efficient procedures are described for the construction of β(1→4)-intergalactosidic linkages up to the hexasaccharide level. Key elements were the use of phenylthio and/or phenyl sulfoxide functionalities for glycosylations and a judiciously designed blocking group pattern for donor and acceptor alike: pivaloyl protection at O-2 for securing β-selectivity, sterically undemanding allyl or benzyl groups at O-3 and O-6 to minimise the steric bulk around the unreactive galactosyl-4-OH, the p-methoxyphenyl moiety, readily replaceable by SPh, as an intermediate anomeric substituent, and an acetyl group for temporary protection of the terminal Gal-4-OH. This strategy lends itself to iterative block synthesis and interchange of donors and acceptors, thereby demonstrating the broad scope and generality of the overall approach. Although predicted by molecular modelling, inclinations towards starch-like coiling could not so far be verified in any of the galacto-tetra-, -penta-, or -hexaoses or their p-methoxyphenyl glycosides.