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2847-00-9

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2847-00-9 Usage

Chemical Properties

colorless very viscous liquid

Uses

1,2:5,6-Di-O-isopropylidene-α-D-ribo-hexofuranose-3-ulose _x000D_(mixture of keto and ketal forms) (cas# 2847-00-9) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 2847-00-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,8,4 and 7 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2847-00:
(6*2)+(5*8)+(4*4)+(3*7)+(2*0)+(1*0)=89
89 % 10 = 9
So 2847-00-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H18O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6,8-10H,5H2,1-4H3/t6-,8-,9-,10-/m1/s1

2847-00-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,2:5,6-Di-O-isopropylidene-α-D-ribo-hexofuranose-3-ulose

1.2 Other means of identification

Product number -
Other names 1,2:5,6-DI-O-ISOPROPYLIDENE-α-D-RIBO-3-HEXULOFURANOSE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2847-00-9 SDS

2847-00-9Downstream Products

2847-00-9Relevant articles and documents

Indirect Electrooxidation by Using Ruthenium Tetraoxide and Chloride Ion as Recycling Mediators. Optimization for the Oxidation of Diisopropylidene-D-glucose to the Ulose

Torii, Sigeru,Inokuchi, Tsutomu,Matsumoto, Shigeaki,Saeki, Takeaki,Oki, Tsunehei

, p. 2108 - 2110 (1989)

Various Various factors related to the yield and selectivity for the indirect electrooxidation of diidopropylidene-glucose (1) to the ulose 2 with ruthenium tetraoxide (RuO4) and chloride ion are investigated.The following is found to be optimum conditions: pH, ca. 10:solvent system, carbon tetrachloride and t-butyl alcohol (ca.9:1); current density, 10-40 mAcm2-; temperature, 20-40 deg C; catalyst amount, 2 molpercent of RuO2.2H2O (based on 1).The optimized electrolysis affords the desired 2 in 90 percent yield along with a trace of the cleavaged product 3 (0.2percent) by an overoxidation.

Mechanistic studies of the biosynthesis of 3,6-dideoxy sugars: Stereochemical analysis of C-3 deoxygenation

Pieper, Patricia A.,Guo, Zhihong,Liu, Hung-Wen

, p. 5158 - 5159 (1995)

-

Synthesis and glycosidase inhibition evaluation of (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol

Zhang, En,Bai, Peng-Yan,Sun, Wei,Wang, Shang,Wang, Ming-Ming,Xu, Shuai-Min,Liu, Hong-Min

, p. 33 - 36 (2016)

A new azasugar (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol (1) was obtained from commercially available D-glucose using one-pot reductive cyclization as a key step. The target product, i.e., the iminosugar isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50?>?100?μM).

Easy and stereoselective approach to α,β-unsaturated γ-lactones fused to pyranoses from furanose scaffolds

Xavier, Nuno M.,Rauter, Amelia P.

, p. 3339 - 3341 (2007)

The first facile and efficient route to pyranose-fused butenolides from furanose scaffolds, convenient for scaling up production, is described. Wittig olefination of 1,2-O-isopropylidene pentofuranos- or hexofuranos-3-uloses with a resonance-stabilized yl

Clode,Horton

, p. 405,407,408 (1970)

Chemoenzymatic Syntheses of Fluoro Sugar Phosphates and Analogues

Drueckhammer, Dale G.,Wong, Chi-Huey

, p. 5912 - 5913 (1985)

Combined chemical and enzymatic procedures are described for the preparation of fluorinated sugar phosphates and analogues.These derivatives are useful for study of sugar metabolism and for synthesis of pharmacological probes in a number of enzymatic systems utilizing sugars.

Synthesis of 3-deoxy-3-C-trifluoromethyl-D-ribose from D-xylose or D-glucose

Lavaire,Plantier-Royon,Portella

, p. 361 - 370 (1996)

The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF3SiMe3 and radical deoxygenation are highly stereoselective.

Synthesis and analysis of a fluorinated product analogue as an inhibitor for 1-deoxy-d-xylulose 5-phosphate reductoisomerase

Munos, Jeffrey W.,Pu, Xiaotao,Liu, Hung-wen

, p. 3090 - 3094 (2008)

1-Deoxy-d-xylulose 5-phosphate (DXP) reductoisomerase (DXR) is an NADPH-dependent enzyme catalyzing the rearrangement and reduction of DXP to methyl-d-erythritol 4-phosphate (MEP). Two mechanisms for this enzymatic reaction have been proposed, involving either an α-ketol rearrangement or a retroaldol/aldol rearrangement. In this study, a fluorinated product analogue, FCH2-MEP, was synthesized as a possible mechanism-based inactivator for DXR if the retroaldol/aldol mechanism is operative. FCH2-MEP was found to be a weak competitive inhibitor, and thus was unable to discriminate between the mechanisms. This result is due to the inability of the targeted enzyme, DXR, to oxidize FCH2-MEP to the aldehyde intermediate that is common to both mechanisms. While FCH2-MEP failed to act as a mechanism-based inactivator, the insight gained from this study will assist in the future design of inhibitors of DXR.

Correlating Hydration Shell Structure with Amino Acid Hydrophobicity

Moore, Jeffrey A.,Parker, Aulma R.,Davisson, V. Jo,Schwab, John M.

, p. 3338 - 3339 (1993)

-

Molar-scale synthesis of 1,2:5,6-Di-0-isopropylidene-α-D- allofuranose: DMSO oxidation of 1,2:5,6-Di-0-isopropylidene-α-D- glucofuranose and subsequent sodium borohydride reduction

Christensen, Signe M.,Hansen, Henrik F.,Koch, Troels

, p. 777 - 780 (2004)

Two variants of oxidation with DMSO followed by sodium borohydride reduction have been investigated to make the synthesis of 1,2:5,6-di-0- isopropylidene-α-D-allofuranose (4) suitable for large-scale manufacturing.

Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2

Kranthikumar, Ramagonolla

supporting information, p. 9833 - 9839 (2021/12/07)

A short and enantioselective synthesis of the 19-epi-BE-43547 A2 chiral framework has been achieved in a high yield. The challenging key C15 tertiary stereocenter was derived from d-glucose. The synthetic strategy involves a Julia-Kocienski olefination to install the lipophilic side chain. An efficient protocol for Z to E isomerization of olefin was developed using a novel UV flow reactor. In addition, an unprecedented oxygen mediated hydroboration and the Krapcho decarboxylation of β-keto lactone were observed. This journal is

Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin

Kienle, Maryline,Eisenring, Patrick,Stoessel, Barbara,Horlacher, Oliver P.,Hasler, Samuel,Van Colen, Gwéna?lle,Hartkoorn, Ruben C.,Vocat, Anthony,Cole, Stewart T.,Altmann, Karl-Heinz

supporting information, p. 1105 - 1131 (2020/03/10)

A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins (minimum inhibitory concentration (MIC) values around 2.5 μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead.

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