138906-42-0

Basic information

• Product Name: p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
• Synonyms: p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS NO: 138906-42-0
• Molecular Weight: 415.4
• Mol File: 138906-42-0.mol

Chemical Properties

• CAS DataBase Reference: p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside(138906-42-0)
• EPA Substance Registry System: p-Methoxyphenyl 2-deoxy-2-phthalimido-β-D-glucopyranoside(138906-42-0)

Safety Data

• Hazardous Substances Data: 138906-42-0(Hazardous Substances Data)

Upstream product

• 150-76-5 4-methoxy-phenol 
• 85-44-9 phthalic anhydride 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 31505-45-0 2-deoxy-2-phthalimido-β-D-glucopyranose 
• 14131-63-6 D-glucosamine hydrochloride 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 

Downstream Products

• 339587-97-2 2-[(2R,4aR,6S,7R,8R,8aS)-2-(4-Allyloxy-3-nitro-phenyl)-8-hydroxy-6-(4-methoxy-phenoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 
• 851385-17-6 2-[(4aR,6S,7R,8R,8aS)-6-(4-Methoxy-phenoxy)-2,2-dimethyl-8-prop-2-ynyloxy-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 
• 803735-10-6 p-methoxyphenyl 4,6-O-diacetyl-2-deoxy-2-phthalimido-3-O-propargyl-β-D-glucopyranoside 
• 851385-31-4 2-[(4aR,6S,7R,8R,8aS)-6-(4-Methoxy-phenoxy)-2,2-dimethyl-8-(3-triisopropylsilanyl-prop-2-ynyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-isoindole-1,3-dione 
• 851385-57-4 Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(4-methoxy-phenoxy)-4-(3-triisopropylsilanyl-prop-2-ynyloxy)-tetrahydro-pyran-3-yl ester 
• 1225290-00-5 p-methoxyphenyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1344980-43-3 p-methoxyphenyl 3,4-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1344980-44-4 p-methoxyphenyl 3,4-di-O-acetyl-6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1448540-28-0 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 
• 1220958-06-4 6-azidohexyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1220958-05-3 6-azidohexyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1448540-29-1 p-methoxyphenyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 
• 1448540-30-4 p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 
• 1448540-31-5 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 

Relevant articles and documents

Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale

A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.

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.

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