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Diaceton-alpha-D-mannofuranose, also known as 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose, is a white to light yellow crystalline powder that serves as a valuable research chemical. It is a derivative of alpha-D-mannofuranose, a monosaccharide that plays a significant role in various biological processes.

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  • 14131-84-1 Structure
  • Basic information

    1. Product Name: Diaceton-alpha-D-mannofuranose
    2. Synonyms: diisopropylidenemannofuranose;Diaceton-alpha-D-mannofuranose;DIACETONE-D-MANNOSE;D-Mannose diacetonide;2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOFURANOSE;2,3:5,6-DI-O-ISOPROPYLIDENE-A-D-MANNOPYRANOSE;(+)-2,3:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE;2,3,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-MANNOFURANOSE
    3. CAS NO:14131-84-1
    4. Molecular Formula: C12H20O6
    5. Molecular Weight: 260.28
    6. EINECS: 1312995-182-4
    7. Product Categories: 13C & 2H Sugars;Biochemistry;O-Substituted Sugars;Sugars;aldehydes;Carbohydrates & Derivatives
    8. Mol File: 14131-84-1.mol
  • Chemical Properties

    1. Melting Point: 125-126 °C (dec.)(lit.)
    2. Boiling Point: 363.54°C (rough estimate)
    3. Flash Point: 171.1 °C
    4. Appearance: White to Off-white/Powder
    5. Density: 1.2377 (rough estimate)
    6. Vapor Pressure: 1.31E-06mmHg at 25°C
    7. Refractive Index: 24 ° (C=1, Acetone)
    8. Storage Temp.: 2-8°C
    9. Solubility: Acetone (Slightly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
    10. PKA: 11.97±0.60(Predicted)
    11. Water Solubility: Soluble in acetone, methanol, water.
    12. Sensitive: Hygroscopic
    13. BRN: 84382
    14. CAS DataBase Reference: Diaceton-alpha-D-mannofuranose(CAS DataBase Reference)
    15. NIST Chemistry Reference: Diaceton-alpha-D-mannofuranose(14131-84-1)
    16. EPA Substance Registry System: Diaceton-alpha-D-mannofuranose(14131-84-1)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 22-24/25-36/37-26
    4. WGK Germany: 3
    5. RTECS:
    6. F: 3-21
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 14131-84-1(Hazardous Substances Data)

14131-84-1 Usage

Uses

Used in Pharmaceutical Industry:
Diaceton-alpha-D-mannofuranose is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential applications in treating various diseases.
Used in Chemical Synthesis:
Diaceton-alpha-D-mannofuranose is used as a synthetic building block for the preparation of complex organic molecules. Its ability to be modified and incorporated into larger structures makes it a valuable tool in the field of organic chemistry.
Used in Research and Development:
As a research chemical, Diaceton-alpha-D-mannofuranose is used in the development of new methodologies and techniques in organic synthesis. It helps researchers understand the reactivity and properties of similar compounds, leading to the discovery of novel applications and advancements in the field.
Used in Synthesis of Ovalicin:
Diaceton-alpha-D-mannofuranose is used as a starting material in the synthesis of ovalicin, a natural product with potential biological activities. Its role in the synthesis process highlights its importance in the development of new pharmaceutical agents.
Used in Synthesis of Hikizimycin Sugar Core:
Diaceton-alpha-D-mannofuranose is also used in the synthesis of the sugar core of hikizimycin, an antibiotic with potent antibacterial properties. Its involvement in the synthesis of such an important compound underscores its utility in the pharmaceutical industry.

Check Digit Verification of cas no

The CAS Registry Mumber 14131-84-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,3 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 14131-84:
(7*1)+(6*4)+(5*1)+(4*3)+(3*1)+(2*8)+(1*4)=71
71 % 10 = 1
So 14131-84-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H20O6/c1-11(2)14-5-6(16-11)7-8-9(10(13)15-7)18-12(3,4)17-8/h6-10,13H,5H2,1-4H3/t6-,7-,8+,9+,10+/m1/s1

14131-84-1 Well-known Company Product Price

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  • TCI America

  • (D2447)  2,3:5,6-Di-O-isopropylidene-D-mannofuranose  >98.0%(GC)

  • 14131-84-1

  • 5g

  • 650.00CNY

  • Detail

14131-84-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,3:5,6-Di-O-isopropylidene-alpha-D-mannofuranose

1.2 Other means of identification

Product number -
Other names 2,3:5,6-Di-O-isopropylidene-α-D-mannofuranose

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:14131-84-1 SDS

14131-84-1Relevant articles and documents

Visible-Light-Induced Pd-Catalyzed Radical Strategy for Constructing C-Vinyl Glycosides

Li, Ming,Qiu, Yi-Feng,Wang, Cui-Tian,Li, Xue-Song,Wei, Wan-Xu,Wang, Yu-Zhao,Bao, Qiao-Fei,Ding, Ya-Nan,Shi, Wei-Yu,Liang, Yong-Min

supporting information, p. 6288 - 6293 (2020/09/02)

A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of C-glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.

Synthesis of Galactosyl-Queuosine and Distribution of Hypermodified Q-Nucleosides in Mouse Tissues

Carell, Thomas,Ensfelder, Timm T.,Heiss, Matthias,Hillmeier, Markus,Kellner, Stefanie,Müller, Markus,Michalakis, Stylianos,Sch?n, Alexander,Scheel, Constanze,Thumbs, Peter,Wagner, Mirko

supporting information, p. 12352 - 12356 (2020/04/27)

Queuosine (Q) is a hypermodified RNA nucleoside that is found in tRNAHis, tRNAAsn, tRNATyr, and tRNAAsp. It is located at the wobble position of the tRNA anticodon loop, where it can interact with U as well as C bases located at the respective position of the corresponding mRNA codons. In tRNATyr and tRNAAsp of higher eukaryotes, including humans, the Q base is for yet unknown reasons further modified by the addition of a galactose and a mannose sugar, respectively. The reason for this additional modification, and how the sugar modification is orchestrated with Q formation and insertion, is unknown. Here, we report a total synthesis of the hypermodified nucleoside galactosyl-queuosine (galQ). The availability of the compound enabled us to study the absolute levels of the Q-family nucleosides in six different organs of newborn and adult mice, and also in human cytosolic tRNA. Our synthesis now paves the way to a more detailed analysis of the biological function of the Q-nucleoside family.

Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators

An, Seungchan,Kim, Gyudong,Kim, Hyun Jin,Ahn, Sungjin,Kim, Hyun Young,Ko, Hyejin,Hyun, Young Eum,Nguyen, Mai,Jeong, Juri,Liu, Zijing,Han, Jinhe,Choi, Hongseok,Yu, Jinha,Kim, Ji Won,Lee, Hyuk Woo,Jacobson, Kenneth A.,Cho, Won Jea,Kim, Young-Mi,Kang, Keon Wook,Noh, Minsoo,Jeong, Lak Shin

, p. 16012 - 16027 (2021/01/09)

Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

Choutka, Jan,Kratochvíl, Michal,Parkan, Kamil,Pohl, Radek,Zyka, Jakub

supporting information, (2020/08/24)

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehy

Total Synthesis of 6-Amino-2,6-dideoxy-α-Kdo from d -Mannose

Ameur, Nassima,Gamboa Marin, Oscar Javier,Gauthier, Charles,Gormand, Paul,Hussain, Nazar,Ravicoularamin, Gokulakrishnan,Sauvageau, Janelle

supporting information, (2020/07/27)

3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-α-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing

Aspartic Acid Forming α-Ketoacid-Hydroxylamine (KAHA) Ligations with (S)-4,4-Difluoro-5-oxaproline

Baldauf, Simon,Bode, Jeffrey W.,Boross, Gábor N.,Ogunkoya, Ayodele O.

, (2020/02/04)

The α-ketoacid-hydroxylamine (KAHA) ligation allows the coupling of unprotected peptide segments. Currently, the most applied hydroxylamine is the 5-membered cyclic hydroxylamine (S)-5-oxaproline, which forms a homoserine ester as the primary ligation product. In order to access native aspartic acid residues at the ligation site, we synthesized a 4,4-difluoro version of this monomer. Upon KAHA ligation, the resulting difluoro alcohol hydrolyzes to an aspartic acid residue with little or no formation of aspartamide. We applied this monomer for the synthesis of the hormone peptides glucagon and an insulin variant, and as well for segment ligation of the peptides UbcH5a and SUMO3.

PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING GLAUCOMA, CONTAINING ADENOSINE DERIVATIVE

-

Paragraph 0126-0130, (2020/02/05)

A pharmaceutical composition for preventing or treating eye diseases and an oral administration agent for preventing or treating eye diseases are provided. The pharmaceutical composition for preventing or treating eye diseases comprises the compound repre

Synthesis of Bioactive Side-Chain Analogues of TAN-2483B

Somarathne, Kalpani K.,McCone, Jordan A. J.,Brackovic, Amira,Rivera, José Luis Pinedo,Fulton, J. Robin,Russell, Euan,Field, Jessica J.,Orme, Christopher L.,Stirrat, Hedley L.,Riesterer, Jasmin,Teesdale-Spittle, Paul H.,Miller, John H.,Harvey, Joanne E.

, p. 1230 - 1237 (2019/02/07)

The fungal metabolite TAN-2483B has a 2,6-trans-relationship across the pyran ring of its furo[3,4-b]pyran-5-one core, which has thwarted previous attempts at its synthesis. We have now developed a chiral pool approach to this core and prepared side-chain

Compound, preparation method and applications thereof, and glycosidase inhibitor

-

Paragraph 0068-0071, (2019/10/01)

The invention relates to the field of enzyme inhibitors, and discloses a compound, a preparation method and applications thereof, and a glycosidase inhibitor, wherein the compound has a structure represented by a formula (I), R is any one selected from hy

Synthesis of Butenolides via a Horner-Wadsworth-Emmons Cascading Dimerization Reaction

Everson, Jack,Kiefel, Milton J.

, p. 15226 - 15235 (2019/11/21)

The efficient synthesis of a range of structurally related butenolides has been observed while we were exploring the substrate-scope of a Horner-Wadsworth-Emmons (HWE) reaction. While aliphatic aldehydes gave the expected HWE product, aromatic aldehydes f

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