80035-32-1

Basic information

• Product Name: Benzyl 2-Deoxy-2-phthalimido--D-glucopyranoside
• Synonyms: Benzyl 2-Deoxy-2-phthalimido--D-glucopyranoside;PhenylMethyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-β-D-glucopyranoside;Benzyl 2-Deoxy-2-phthalimido-2-D-glucopyranoside (~90%)
• CAS NO: 80035-32-1
• Molecular Formula: C₂₁H₂₁NO₇
• Molecular Weight: 399.39394
• Product Categories: Carbohydrates & Derivatives
• Mol File: 80035-32-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 158-163°C
• Boiling Point: 626.739°C at 760 mmHg
• Flash Point: 332.84°C
• Appearance: /
• Density: 1.497g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.683
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.95±0.70(Predicted)
• CAS DataBase Reference: Benzyl 2-Deoxy-2-phthalimido--D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-Deoxy-2-phthalimido--D-glucopyranoside(80035-32-1)
• EPA Substance Registry System: Benzyl 2-Deoxy-2-phthalimido--D-glucopyranoside(80035-32-1)

Safety Data

• Hazardous Substances Data: 80035-32-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C21H21NO7/c23-10-15-17(24)18(25)16(21(29-15)28-11-12-6-2-1-3-7-12)22-19(26)13-8-4-5-9-14(13)20(22)27/h1-9,15-18,21,23-25H,10-11H2/t15?,16?,17-,18-,21-/m1/s1

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 33868-53-0 tributylstannyl benzyl ether 
• 100-51-6 benzyl alcohol 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 7772-87-4 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 

Downstream Products

• 80035-33-2 benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 149342-15-4 benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 174360-42-0 benzyl 2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranoside 
• 1221126-96-0 benzyl 2-deoxy-2-phthalimido-β-D-gluco-hexodialdo-1,5-pyranoside 
• 156520-24-0 Benzyl 3-O-benzyl-2-desoxy-4,6-O-isopropylidene-2-phthalimido-β-D-glucopyranoside 
• 156520-27-3 Benzyl 2-allyloxycarbonylamino-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranoside 
• 330999-05-8 Benzyl 3,6-di-O-benzyl-2-deoxy-2-amino-β-D-glucopyranoside 
• 80035-36-5 benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 
• 165248-13-5 Acetic acid (4aR,6R,7R,8R,8aS)-6-benzyloxy-7-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 151266-85-2 benzyl 3-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 174360-45-3 benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranoside 
• 174360-46-4 benzyl O-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-3-O-acetyl-2-deoxy-2-phthalimido-6-O-trimethylacetyl-β-D-glucopyranoside 
• 191216-69-0 Succinic acid (2R,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-hydroxy-tetrahydro-pyran-4-yl ester (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Synthesis of N -acetyl glucosamine analogs as inhibitors for hyaluronan biosynthesis

Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon incubation with pancreatic cancer cells, a fluorine-containing glucosamine analog was found to exhibit significant inhibitory activities of hyaluronan synthesis. Furthermore, it drastically reduced the proliferation of cancer cells. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.

Chemical Synthesis of Nod-Rm-1: the Nodilation Factor Involved in Rhizobium meliloti-legume Symbiosis

A total synthesis of the sulfated lipotetrasaccharide (NodRm-1) is described.First, the disaccharide glycosyl donor - O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl chloride 3a or

RECTIVITE COMPAREE DE DIVERS ACCEPTEURS DE LA D-GLUCOSAMINE LORS DE LA SYNTHESE DE PRECURSEURS DU CHITOBIOSE

Six D-glucosamine derivatives, diversely substituted at the nitrogen atom, were tested as acceptors in glycosylation reactions with 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose (1) as the donor and trimethylsilyl trifluoromethanesulfonate as the promoter.The observed yields were high with 2-phthalimido- and 2-azido-D-glucosamine acceptors and more generally good with acceptors of the 1,6-anhydro-D-glucosamine series.The disaccharides benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (20), benzyl 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (21), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (22), 4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-2-allyloxycarbonylamino-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (23), 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (24) and 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-1,6-anhydro-3-O-benzyl-2-deoxy-β-D-glucopyranose (25) have thus been synthesized.