114853-29-1

Basic information

• Product Name: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside
• Synonyms: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside;Allyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside;Allyl 2-deoxy-2-phthalimido-b-D-glucopyranoside;Allyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2-D-glucopyranoside
• CAS NO: 114853-29-1
• Molecular Formula: C₁₇H₁₉NO₇
• Molecular Weight: 349.33526
• Product Categories: Carbohydrates & Derivatives
• Mol File: 114853-29-1.mol

Chemical Properties

• Appearance: /
• Refractive Index: 1.646
• Solubility: Methanol
• CAS DataBase Reference: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside(114853-29-1)
• EPA Substance Registry System: 2-Propenyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)--D-glucopyranoside(114853-29-1)

Safety Data

• Hazardous Substances Data: 114853-29-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Brown Solid

InChI:InChI=1/C17H19NO7/c1-2-7-24-17-12(14(21)13(20)11(8-19)25-17)18-15(22)9-5-3-4-6-10(9)16(18)23/h2-6,11-14,17,19-21H,1,7-8H2/t11?,12?,13-,14-,17-/m1/s1

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 85-44-9 phthalic anhydride 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 72333-26-7 allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 

Downstream Products

• 114853-35-9 allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 215102-67-3 allyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-glucopyranoside 
• 114853-30-4 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 114853-36-0 Acetic acid (2R,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 107802-81-3 allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-3)>-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside 
• 107802-79-9 allyl O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside 
• 107802-78-8 allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-3)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside 
• 107802-83-5 O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1-> 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 
• 107802-77-7 allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-6-O-benzyl-2-deoxy-2-phtalimido-β-D-glucopyranoside 
• 107823-72-3 allyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 153804-92-3 allyl 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 158420-88-3 4-O-(2'-azido-3',4',6'-tri-O-benzyl-2'-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 158420-83-8 allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 158420-85-0 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 

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.

SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCOCCUS VACCINE

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SYNTHETIC OLIGOSACCHARIDES FOR STAPHYLOCCOCUS VACCINE

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