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B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois a protected glucopyranoside that serves as a building block for the synthesis of complex carbohydrates. B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiofeatures β-phenylthio, 2 and 3 benzyl, and 4,6-benzylidine protecting groups, which play a crucial role in the synthesis process.

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  • 87470-70-0 Structure
  • Basic information

    1. Product Name: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-
    2. Synonyms: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-;Beta-D-Glucopyranoside,phenyl2,3-bis-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-
    3. CAS NO:87470-70-0
    4. Molecular Formula: C33H32O5S
    5. Molecular Weight: 540.677
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 87470-70-0.mol
  • Chemical Properties

    1. Melting Point: 143-144 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
    2. Boiling Point: 675.3±55.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.27±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: 2-8°C
    8. Solubility: N/A
    9. CAS DataBase Reference: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(CAS DataBase Reference)
    10. NIST Chemistry Reference: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(87470-70-0)
    11. EPA Substance Registry System: B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-(87470-70-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 87470-70-0(Hazardous Substances Data)

87470-70-0 Usage

Uses

Used in Pharmaceutical Industry:
B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois used as a building block for the synthesis of complex carbohydrates in the pharmaceutical industry. The presence of β-phenylthio, 2 and 3 benzyl, and 4,6-benzylidine protecting groups allows for the creation of intricate carbohydrate structures that can be utilized in the development of new drugs and therapies.
Used in Chemical Research:
In the field of chemical research, B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois used as a valuable building block for the synthesis of complex carbohydrates. Researchers can leverage the compound's protecting groups to explore new methods and techniques in carbohydrate chemistry, potentially leading to breakthroughs in various applications.
Used in Material Science:
B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois also used in material science for the development of advanced materials with unique properties. B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-'s protecting groups enable the synthesis of complex carbohydrate structures that can be incorporated into materials with specific characteristics, such as improved biocompatibility or enhanced functionality.
Overall, B-D-Glucopyranoside, phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thiois a versatile compound with a wide range of applications across various industries, including pharmaceuticals, chemical research, and material science. Its unique structure and protecting groups make it an invaluable building block for the synthesis of complex carbohydrates and the development of innovative products and solutions.

Check Digit Verification of cas no

The CAS Registry Mumber 87470-70-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,7,4,7 and 0 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 87470-70:
(7*8)+(6*7)+(5*4)+(4*7)+(3*0)+(2*7)+(1*0)=160
160 % 10 = 0
So 87470-70-0 is a valid CAS Registry Number.

87470-70-0SDS

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 B-D-Glucopyranoside,phenyl2,3-bis-O-(phenylmethyl)-4,6-O-[(R)-phenylmethylene]-1-thio-

1.2 Other means of identification

Product number -
Other names (2,3-Dibrom-propyl)-phenyl-sulfon

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:87470-70-0 SDS

87470-70-0Relevant articles and documents

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

Hansen, Thomas,Ofman, Tim P.,Vlaming, Joey G. C.,Gagarinov, Ivan A.,van Beek, Jessey,Goté, Tessa A.,Tichem, Jacoba M.,Ruijgrok, Gijs,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.

supporting information, p. 937 - 945 (2020/12/09)

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

Reagent controlled stereoselective synthesis of teichoic acid α-(1,2)-glucans

Berni, Francesca,Enotarpi, Jacopo,Overkleeft, Hermen S.,Van Der Marel, Gijs,Wang, Liming,Codée, Jeroen D. C.

, p. 2038 - 2050 (2020/03/27)

The stereoselective construction of 1,2-cis-glycosidic linkages is key in the assembly of biologically relevant glycans, but remains a synthetic challenge. Reagent-controlled glycosylation methodologies, in which external nucleophiles are employed to modu

Conformationally Switchable Glycosyl Donors

Holmstr?m, Thomas,Pedersen, Christian Marcus

, p. 13242 - 13251 (2019/11/03)

Glycosyl donors functionalized with 2,2′-bipyridine moieties on the 3-OH and 6-OH or the 2-OH and 4-OH undergo a conformational change when forming 1:1 complexes with Zn2+ ions. The pyranoside ring of the zinc complexes adopted axial-rich skew boat conformations. The reactivities of the two glycosyl donors were investigated by performing a series of glycosylations in the presence or absence of Zn2+ ions. These glycosylations suggested a decrease in reactivity when binding Zn2+. The conformational effect of binding Zn2+ was therefore studied using a third glycosyl donor, unable to undergo conformational changes when binding Zn2+. From competition experiments, it was observed that the binding-induced conformational change increased the reactivity slightly compared to the glycosyl donor unable to undergo a conformational change.

Glycosyl Fluorides as Intermediates in BF3·OEt2-Promoted Glycosylation with Trichloroacetimidates

Nielsen, Michael M.,Stougaard, Bolette A.,Bols, Mikael,Glibstrup, Emil,Pedersen, Christian M.

supporting information, p. 1281 - 1284 (2017/03/17)

Glycosyl fluorides have been found to be important intermediates in glycosylations with trichloroacetimidate donors and BF3·OEt2 activation (0.2–1 equiv.). Low-temperature NMR spectroscopy experiments revealed that the α-trichloroacetimidate was transformed into the glycosyl fluoride with inversion of stereochemistry, whereas the β anomer was not. A concerted mechanism was suggested for the stereospecific formation of glycosyl fluorides, which is not accounted for in the classic mechanism.

Borinic Acid Catalyzed Stereo- and Regioselective Couplings of Glycosyl Methanesulfonates

D'Angelo, Kyan A.,Taylor, Mark S.

, p. 11058 - 11066 (2016/09/12)

In the presence of a diarylborinic acid catalyst, glycosyl methanesulfonates engage in regio- and stereoselective couplings with partially protected pyranoside and furanoside acceptors. The methanesulfonate donors are prepared in situ from glycosyl hemiacetals, and are coupled under mild, operationally simple conditions (amine base, organoboron catalyst, room temperature). The borinic acid catalyst not only influences site-selectivity via activation of 1,2- or 1,3-diol motifs, but also has a pronounced effect on the stereochemical outcome: 1,2-trans-linked disaccharides are obtained selectively in the absence of neighboring group participation. Reaction progress kinetic analysis was used to obtain insight into the mechanism of glycosylation, both in the presence of catalyst and in its absence, while rates of interconversion of methanesulfonate anomers were determined by NMR exchange spectroscopy (EXSY). Together, the results suggest that although the uncatalyzed and catalyzed reactions give rise to opposite stereochemical outcomes, both proceed by associative mechanisms.

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Baek, Ju Yuel,Kwon, Hea-Won,Myung, Se Jin,Park, Jung Jun,Kim, Mi Young,Rathwell, Dominea C.K.,Jeon, Heung Bae,Seeberger, Peter H.,Kim, Kwan Soo

, p. 5315 - 5320 (2015/07/15)

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

Synthesis and reactivity of 4'-deoxypentenosyl disaccharides

Padungros, Panuwat,Fan, Ren-Hua,Casselman, Matthew D.,Cheng, Gang,Khatri, Hari R.,Wei, Alexander

, p. 4878 - 4891 (2014/06/23)

4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4'-deoxypentenosyl (4'-DP) disaccharides, and we investigate their post-glycosylational C5' additions using the DMDO oxidation/ring-opening sequence. The α-linked 4'-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf2O activation, whereas β-linked 4'-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4'-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochemical configuration of the terminal 4'-DP unit is established at a post-glycosylative stage.

A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity

Blom, Petra,Ruttens, Bart,Van Hoof, Steven,Hubrecht, Idzi,Van Der Eycken, Johan,Sas, Benedikt,Van Hemel, Johan,Vandenkerckhove, Jan

, p. 10109 - 10112 (2007/10/03)

An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

Chemistry of 4,6-O-benzylidene-D-glycopyranosyl triflates: Contrasting behavior between the gluco and manno series

Crich, David,Cai, Weiling

, p. 4926 - 4930 (2007/10/03)

Activation of either anomer of S-phenyl 2,3-di-O-benzyl-4,6-O- benzylidene-1-deoxy-1-thia-D-glucopyranoside with triflic anhydride in dichloromethane at -78 °C in the presence of 2,6-di-tert-butyl-4- methylpyridine affords a highly active glycosylating species which, on addition of alcohols, provides α-glucosides with high selectivity. This selectivity stands in stark contrast to the analogous mannopyranoside series, which affords the β-mannosides with excellent selectivity under the same conditions. Low-temperature NMR experiments support the notion that a glucosyl triflate is formed in the initial activation step. Possible reasons for the diverging stereoselectivity in the gluco and manno series are discussed.

Capsular polysaccharide of Streptococcus pneumoniae type 19F: Synthesis of the repeating unit

Bousquet, Ennio,Khitri, Malika,Lay, Luigi,Nicotra, Francesco,Panza, Luigi,Russo, Giovanni

, p. 171 - 181 (2007/10/03)

A new and more versatile synthesis of β-d-ManpNAc-(1→4)-α-d-Glcp-(1→2)-α-l-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages. Copyright (C) 1998 Elsevier Science Ltd. A new and more versatile synthesis of β-D-ManpNAc-(1→4)-α-D-Glcp-(1→2)-α-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages.

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