13964-21-1

Basic information

• Product Name: 1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-a-D-allofuranose
• Synonyms: 1,2:5,6-Bis-O-(1-Methylethylidene)-α-D-allofuranose 3-(4-Methylbenzenesulfonate);1,2:5,6-Di-O-isopropylidene-α-D-allofuranose p-Toluenesulfonate;1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose;3-O-(4-Methylphenylsulfonyl)-1-O,2-O:5-O,6-O-bis(1-methylethylidene)-α-D-allofuranose;4-Methylbenzenesulfonic acid 1-O,2-O:5-O,6-O-bis(isopropylidene)-3-deoxy-α-D-allofuranos-3-yl ester
• CAS NO: 13964-21-1
• Molecular Formula: C₁₉H₂₆O₈S
• Molecular Weight: 0
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 13964-21-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 120-121°C
• Boiling Point: 511.3°Cat760mmHg
• Flash Point: 263°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 4.62E-10mmHg at 25°C
• Refractive Index: 1.567
• Solubility: Dichloromethane, Ether, Ethyl Acetate, Methanol
• CAS DataBase Reference: 1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-a-D-allofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-a-D-allofuranose(13964-21-1)
• EPA Substance Registry System: 1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-a-D-allofuranose(13964-21-1)

Safety Data

• Hazardous Substances Data: 13964-21-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

1,2:5,6-Di-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose (cas# 13964-21-1) is a compound useful in organic synthesis.

InChI:InChI=1/C19H26O8S/c1-11-6-8-12(9-7-11)28(20,21)27-15-14(13-10-22-18(2,3)24-13)23-17-16(15)25-19(4,5)26-17/h6-9,13-17H,10H2,1-5H3

Upstream product

• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 98-59-9 p-toluenesulfonyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 (3aR,5S,6S,6aR)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 536-57-2 p-toluene sulfinic acid 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 2595-05-3 Diacetone D-glucose 
• 79378-73-7 1,2:5,6-Di-O-isopropyliden-3-O-(p-tolylsulfinyl)-α-D-allofuranose 

Downstream Products

• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 7508-81-8 [(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 214918-32-8 [(3aR,5S,6S,6aR)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 37073-89-5 [(3aR,5S,6S,6aR)-5-((R)-1,2-Dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 214918-31-7 [(3aR,5S,6S,6aR)-5-((S)-1-Hydroxy-2-iodo-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester 
• 451505-53-6 Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-benzyloxycarbonylamino-6-methyl-tetrahydro-pyran-3-yl ester 
• 451505-46-7 Toluene-4-sulfonic acid (R)-2-((3aR,5S,6S,6aR)-6-benzyloxycarbonylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester 
• 214918-34-0 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester 
• 16848-19-4 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 28251-83-4 1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose 
• 1220113-65-4 5-formyl-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-6-yl 4 methylbenzenesulfonate 
• 141903-85-7 3β-<((trifluoromethyl)phenylmethyl)imino>-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose 
• 141903-84-6 3-((4-methoxyphenyl)telluro)-3-deoxy-1,2:5,6-di-O-isopropylidene-D-glucofuranose 

Relevant articles and documents

Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation

N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NM

Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.

Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium

In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.