65371-16-6

Basic information

• Product Name: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
• Synonyms: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE;6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE;6-Azido-6-deoxzy-1,2-o-isopropylidene-a-D-glucofuranose;6-Azido-6-deoxy-1,2-O-(1-Methylethylidene)-α-D-glucofuranose
• CAS NO: 65371-16-6
• Molecular Formula: C₉H₁₅N₃O₅
• Molecular Weight: 245.23
• Product Categories: Carbohydrates & Derivatives
• Mol File: 65371-16-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 101-103°C
• Appearance: White crystalline solid
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE(65371-16-6)
• EPA Substance Registry System: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE(65371-16-6)

Safety Data

• Hazardous Substances Data: 65371-16-6(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C9H15N3O5/c1-9(2)16-7-5(14)6(15-8(7)17-9)4(13)3-11-12-10/h4-8,13-14H,3H2,1-2H3/t4?,5-,6-,7+,8-/m1/s1

Upstream product

• 33557-25-4 1,2-O-isopropylidene-α-D-glucofuranos-6-yl methanesulfonate 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 78633-09-7 3-O-acetyl-6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 20847-05-6 6-Azido-6-desoxy-D-glucopyranose 
• 67-64-1 acetone 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 19189-68-5 3-O-acetyl-1,2-O-isopropylidene-6-O-tosyl-D-glucofuranose 

Downstream Products

• 24384-87-0 6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 20847-05-6 6-Azido-6-desoxy-D-glucopyranose 
• 121195-24-2 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant articles and documents

TOTAL SYNTHESIS OF THE DISACCHARIDE OF BLEOMYCIN, 2-O-(α-D-MANNOPYRANOSYL)-L-GULOPYRANOSE

2-O-(Α-D-Mannopyranosyl)-L-gulapyranose, the sugar portion of bleomycin has been synthesized.

6-Azido-6-deoxy-l-idose as a Hetero-Bifunctional Spacer for the Synthesis of Azido-Containing Chemical Probes

The design of 6-azido-6-deoxy-l-idose for use as a hetero-bifunctional spacer is reported. The hemiacetal at one terminus is an equivalent of an aldehyde and can react with nucleophiles, such as amino groups and electron-rich aromatics. The azido group at the other terminus bio-orthogonally undergoes a Hüisgen [3+2] cycloaddition with an acetylene. The idose derivative exhibited a higher level of reactivity towards oxime formation than a corresponding glucose derivative. The13C NMR spectrum of the uniformly13C-labeled 6-azido-idose indicated that the acyclic forms of the sugar totaled 0.3 % of all the isomers, whereas those of glucose totaled 0.01 %. The larger population of the acyclic forms of the idose derivative would result in higher reactivity towards electrophilic addition in comparison with glucose derivatives. Finally, we prepared a C-idosyl epigallocatechin gallate (EGCG) that bears an azido group through C-glycosylation of EGCG with 6-azido-idose. This glycosyl form of the C-idosyl EGCG exhibited a cytotoxicity against U266 cells that was comparable to that of EGCG. These results suggested that the EGCG derivative could be used as an effective chemical probe for the elucidation of EGCG biological functions.

A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S,3R,4R,5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE

Deoxymannojirimycin may be prepared in moderate amounts in an overall yield of 35percent in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar.A synthesis of (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is reported.