159734-70-0

Basic information

• Product Name: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside
• Synonyms: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside
• CAS NO: 159734-70-0
• Molecular Weight: 581.689
• Mol File: 159734-70-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside(159734-70-0)
• EPA Substance Registry System: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside(159734-70-0)

Safety Data

• Hazardous Substances Data: 159734-70-0(Hazardous Substances Data)

Upstream product

• 617-86-7 triethylsilane 
• 208644-70-6 phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-39-0 benzyl bromide 
• 136882-36-5 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 
• 127061-09-0 phenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 79528-49-7 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 108-98-5 thiophenol 

Downstream Products

• 254444-23-0 phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1614235-80-1 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1614235-81-2 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1614235-76-5 phenyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1373883-54-5 C₄₆H₅₃NO₆SSi 
• 80035-36-5 benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 
• 1228931-48-3 C₃₆H₃₃NO₆S₃ 
• 208644-71-7 methyl 2,4-di-O-benzyl-3-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside 
• 208644-73-9 methyl 2,4-di-O-benzyl-3-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-L-fucopyranoside 
• 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 
• 185797-97-1 O-(3-O-acetyl-4,6-O-benzylidene-2-chloroacetyl-β-D-glucopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide 
• 185797-98-2 O-(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosylazide 
• 161315-67-9 O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 161315-68-0 O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Relevant articles and documents

Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide

A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.

Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52

We report here a strategy for the synthesis of N-linked glycopeptide analogues that replace the glycosidic linkages extending from the core pentasaccharide with thioethers amenable to construction by chemoselective ligation. The key building block, a pent