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

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

• 108-98-5 thiophenol 
• 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 
• 79528-49-7 phenyl 3,4,6-tri-O-acetyl-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 

Downstream Products

• 159734-75-5 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 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 
• 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 
• 161315-65-7 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 161315-66-8 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.

Hafnium(IV) tetratriflate in selective reductive carbohydrate benzylidene acetal opening reaction and direct silylation reaction

Hafnium(IV) tetratriflate was shown to be an effective catalyst for the regioselective reductive benzylidene ring opening with concurrent silylation reaction. The synthetic conditions were optimized, and the scope and limitations were identified. In addit

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

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.