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1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE is a complex organic compound derived from xylose, a five-carbon sugar. It is characterized by its unique structure, which includes an isopropylidene group and a furanose ring. 1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE has potential applications in various fields due to its chemical properties and reactivity.

53167-11-6

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  • (3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

    Cas No: 53167-11-6

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53167-11-6 Usage

Uses

Used in Pharmaceutical Industry:
1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE is used as a reagent for the intramolecular cyclization of alkoxyamino-sugars. This process is crucial in the preparation of glycosidase inhibitors, which are important compounds in the development of drugs targeting various diseases, including cancer and infectious diseases.
1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE's ability to participate in the synthesis of glycosidase inhibitors makes it a valuable tool in the pharmaceutical industry, where it can contribute to the development of novel therapeutic agents. By facilitating the production of these inhibitors, 1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLO-PENTODIALDO-1,4-FURANOSE plays a significant role in advancing medical research and drug discovery.

Check Digit Verification of cas no

The CAS Registry Mumber 53167-11-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,1,6 and 7 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 53167-11:
(7*5)+(6*3)+(5*1)+(4*6)+(3*7)+(2*1)+(1*1)=106
106 % 10 = 6
So 53167-11-6 is a valid CAS Registry Number.

53167-11-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name (3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde

1.2 Other means of identification

Product number -
Other names 5-Aldo-1,2-O-isopropylidene-a-D-xylofuranose

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:53167-11-6 SDS

53167-11-6Downstream Products

53167-11-6Relevant articles and documents

Synthesis of a truncated tetradenolide

Dávila García, álvaro,Bernès, Sylvain,Sartillo-Piscil, Fernando,Meza-León, Rosa Luisa

, p. 4373 - 4379 (2020)

The enantiopure synthesis of a truncated tetradenolide is presented. Starting from the versatile Chiron 7,3-lactone-xylofuranose derivative (7,3-LXF), the enantiomerically pure synthesis of the title compound is obtained in six steps with a 40% overall yield.

Synthesis and biological evaluation of 1,5-dideoxy-1,5-iminoxylitol-Aamino acid hybrids as xylosidase inhibitors

Steiner, Andreas J.,Stuetz, Arnold E.,Tarling, Chris A.,Withers, Stephen G.,Wrodnigg, Tanja M.

, p. 553 - 557 (2009)

1,5-Dideoxy-1,5-iminoxylitolamino acid hybrids have been synthesized by cyclisation via a double reductive amination of xylo-pentodialdose and the respective amino groups of lysine as well as serine components. Further modification with aromatic substituents gave access to lipophilic derivatives. Kinetic studies revealed that all compounds exhibited better inhibitory properties against β-xylosidase from Thermoanaerobacterium sacharolyticum than the parent iminosugar.

Asymmetric synthesis and biological evaluation of (+)-cardiobutanolide, (?)-3-deoxycardiobutanolide and analogues as antiproliferative agents

Kova?evi?, Ivana,Kesi?, Jelena,Popsavin, Mirjana,Francuz, Jovana,Koji?, Vesna,Jakimov, Dimitar,Rodi?, Marko V.,Zelenovi?, Bojana Sre?o,Benedekovi?, Goran,Popsavin, Velimir

supporting information, (2021/08/30)

Two natural products, (+)-cardiobutanolide and (?)-3-deoxycardiobutanolide, as well as five new analogues, were synthesized in several steps that included zinc-mediated THF ring opening, subsequent stereoselective olefination, and final Sharpless asymmetric dihydroxylation. In vitro antitumour activities of these compounds were evaluated against a panel of eight human tumour cell lines and one normal cell line. Some of compounds displayed powerful effects against tumour cells, but none of them were active toward normal cells. A SAR study revealed that the change of configuration at the C-6 and C-7 position of (+)-cardiobutanolide decreases antitumour activity of analogues. It also appears that the presence of a hydroxyl group at the C-3 position increases the activity of this type of lactones. A comparison of activities of conformationally rigid lactone goniofufurone with that of more flexible cardiobutanolide and 3-deoxycardiobutanolide indicates that steric flexibility has a positive effect on cytotoxicity. It was also confirmed that removal of the phenyl group may result in analogues of higher activity. Flow cytometry analysis revealed that the synthesized compounds did not induce apoptosis and necrosis of K562 cells. However, Western blot analysis showed that all compounds but one had an increased Bax/Bcl-2 protein expression ratio.

Method for preparing eribulin and intermediate thereof

-

Paragraph 0128-0130, (2018/09/08)

The present invention relates to a method for preparing eribulin and an intermediate thereof. In particular, the invention relates to a method for preparing a compound of formula 5, R3 is selected from aldehyde or OR1, n=0 or 1, R1 is a hydroxy protecting group, and preferably the hydroxy protecting group is selected from tert-butyldimethylsilyl, tert-butyldiphenylsilyl, p-methoxybenzyl or benzyl.The invention also provides a method for preparing halichondrin and derivatives thereof such as the eribulin from the compound of formula 5.

Thermal and Lewis acid promoted intramolecular Diels-Alder reaction of furanose tethered 1,3,9-decatriene systems: A synthetic and computational investigation

Kalmode, Hanuman P.,Maity, Dilip K.,Bhate, Prakash M.

, p. 63445 - 63462 (2016/07/19)

The intramolecular Diels-Alder (IMDA) reaction of furanose tethered 1,3,9-decatrienes (4a-4r) was investigated under thermal conditions and in the presence of a Lewis acid. The stereoselectivity was determined by establishing the structures of adducts through single crystal X-ray diffraction and 1H NMR spectroscopy. It was found that contrary to expectations, the thermal IMDA reaction of (3E) and (3Z)-1,3,9-decatrienes proceeded with nearly equal rate and furnished IMDA adducts (6-25) with moderate stereoselectivity. In some cases, rearranged products (9, 12, 17 and 24) arising out of a 1,5-sigmatropic shift, cis-trans isomerization followed by IMDA reaction were formed. In contrast, a Lewis acid promoted IMDA reaction afforded only one adduct albeit in lower yields. Not surprisingly, cis-boat transition states were favored over trans-boat transition states. Experimental results were corroborated with transition state modeling of these reactions by applying density functional theory based electronic structure calculations.

General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

Mulani, Shaheen K.,Cheng, Kuang-Chun,Mong, Kwok-Kong T.

supporting information, p. 5536 - 5539 (2015/12/01)

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

Conformationally constrained goniofufurone mimics as inhibitors of tumour cells growth: Design, synthesis and SAR study

Benedekovi?, Goran,Francuz, Jovana,Kova?evi?, Ivana,Popsavin, Mirjana,Sre?o Zelenovi?, Bojana,Koji?, Vesna,Bogdanovi?, Gordana,Divjakovi?, Vladimir,Popsavin, Velimir

supporting information, p. 449 - 458 (2014/07/07)

Synthesis of conformationally restricted (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2) analogues, with embedded O-isopropylidene, O-methylidene or cyclic carbonate functions is disclosed starting from d-glucose. A number of potential bioisosteres

Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

O?a, Noe,Romero-Carrasco, Antonio,Pino-González, M. Soledad

, p. 156 - 163 (2013/04/10)

Epoxyamides obtained from d-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was

Total synthesis of herbicidin C and aureonuclemycin: Impasses and new avenues

Hager, Dominik,Paulitz, Christian,Tiebes, Joerg,Mayer, Peter,Trauner, Dirk

, p. 10784 - 10801 (2013/11/19)

The undecose nucleoside antibiotics herbicidin C and aureonuclemycin are biologically highly active and represent challenging targets for total synthesis. Herein, the gradual evolution of our synthetic strategy toward these natural products is described in detail. The initial route encompasses metalate addition chemistry but suffers from poor stereochemical control. In contrast, the ultimately successful strategy benefits from a variety of reagent-controlled stereoselective transformations, including a surprisingly facile and highly diastereoselective N-glycosylation process. The presented work also describes new building blocks that might find further application in carbohydrate chemistry.

Lewis acid-assisted olefin cross-metathesis reaction: An efficient approach for the synthesis of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin and evaluation of their antitumor activity

Nagarapu, Lingaiah,Gaikwad, Hanmant K.,Bantu, Rajashaker,Ganesh Kumar,Pombala, Sujitha

supporting information; scheme or table, p. 1287 - 1291 (2012/03/27)

A series of glycosidic-pyrroloquinolinone based novel building blocks of camptothecin (2a-g) were synthesized via Lewis acid-assisted olefin cross-metathesis reaction using Ti(OiPr)4 30 mol % and 10 mol % of Grubb's second generation catalyst with good to excellent yields. Most of these compounds exhibited significant growth inhibitory effects on all the tested cancer cell lines and three compounds (2c, 2d and 2e) showed potent cytotoxic activity.

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