24877-07-4

Basic information

• Product Name: Acetic acid (3R,4R,5R,6S)-3,5-diacetoxy-2-bromo-6-methyl-tetrahydro-pyran-4-yl ester
• CAS NO: 24877-07-4
• Molecular Weight: 353.167
• Mol File: 24877-07-4.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid (3R,4R,5R,6S)-3,5-diacetoxy-2-bromo-6-methyl-tetrahydro-pyran-4-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (3R,4R,5R,6S)-3,5-diacetoxy-2-bromo-6-methyl-tetrahydro-pyran-4-yl ester(24877-07-4)
• EPA Substance Registry System: Acetic acid (3R,4R,5R,6S)-3,5-diacetoxy-2-bromo-6-methyl-tetrahydro-pyran-4-yl ester(24877-07-4)

Safety Data

• Hazardous Substances Data: 24877-07-4(Hazardous Substances Data)

Upstream product

• 73-34-7 D-Fucose 
• 108-24-7 acetic anhydride 
• 28161-52-6 (2R,3R,4S,5R,6R)-6-Methyl-tetrahydro-pyran-2,3,4,5-tetraol 
• 1187858-70-3 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 7404-35-5 Acetic acid (3R,4R,5R,6S)-2,3,5-triacetoxy-6-methyl-tetrahydro-pyran-4-yl ester 
• 73-34-7 6-deoxy-L-talopyranoe 
• 643-17-4 α-D-rhamnopyranose 
• 64-19-7 acetic acid 
• 4026-27-1 1,2:3,4-di-O-isopropylidene-α-D-fucopyranose 
• 34371-41-0 1,2,3,4-tetra-O-acetyl-6-deoxy-β-D-galactopyranose 
• 51921-33-6 1,2,3,4-tetra-O-acetyl-D-fucopyranose 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-6-deoxy-α-D-galactopyranose 

Downstream Products

• 125135-31-1 1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranose 
• 124477-14-1 phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexapyranosyl)-1-thio-β-D-glucopyranoside 
• 125085-11-2 phenyl 4-O-(2-O-acetyl-3,4-di-O-benzyl-6-deoxy-β-D-glucopyranosyl)-2,3-di-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 
• 129081-04-5 (3aR,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-2-ethoxy-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 
• 93414-06-3 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4-tri-O-acetyl-β-D-fucopyranosyl)-α-D-galactopyranoside 
• 180471-90-3 8-methoxycarbonyloctyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 482648-35-1 phenylmethyl 2,3,4-triacetyl-β-D-fucopyranoside 
• 1055028-78-8 C₄₃H₆₀O₁₄ 
• 850894-52-9 ipomoeassin B 
• 1055034-37-1 2-methyl-but-2-enoic acid 3-(tert-butyl-dimethyl-silanyloxy)-5-[3-(dimethyl-phenyl-silanyl)-3-phenyl-acryloyloxy]-6-hydroxymethyl-2-[2,2,4-trimethyl-6-(1-propyl-but-3-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-4-yl ester 
• 1053260-83-5 C₄₅H₆₂O₁₆ 
• 850894-55-2 ipomoeassin E 
• 929682-63-3 C₅₈H₈₂O₁₃Si₂ 
• 929682-67-7 C₅₇H₈₄O₁₄Si₂ 

Relevant articles and documents

Halogenation and anomerization of glycopyranoside by TESH/bromine and BHQ/bromine

Treatment of peracetylated glycosides and β-isopropyl glycosides with halogen in the presence of TESH and BHQ has been found to result in the halogenation and the anomerization, respectively. Peracetylatedglycosides treaded with I2/TESH or Br2/TESH leading tothe formation of corresponding glycosyl halides, and b-isopropyl glycosidesreacted with Br2/BHQ resulting in the formation of a-glycosides. The anomerizationof glycosidic bond was considered to be catalyzed by in situ formation of hydrogenbromide from the mixing of Br2/BHQ.

Neuroprotective activity of different monosaccharide-modified gastrodin analogs

Gastrodin is a very important and well-known bioactive glycoside compound in Chinese medicine. It is also known as a drug with neuroprotective function. Here, a practical diversified synthesis of a series of gastrodin analogs was reported, which involved four-step procedures consisting of bromination, oxidation, etherification, and reduction. Various gastrodin analogs were obtained in good yields. The compound 4c in this study has a good neuroprotective function: it can significantly downregulate tumor necrosis factor-α and inducible nitric oxide synthase protein levels. The results of this study can provide a research basis for the development of neuroprotective drugs.

Total Syntheses of Resin Glycosides Murucoidins IV and v

Murucoidins IV and V, two bioactive resin glycosides with complex yet similar structures isolated from the morning glory family, were synthesized in a convergent manner. All of the glycosylations in these syntheses including the key [3 + 2] coupling were

Organoboron-Promoted Regioselective Glycosylations in the Synthesis of a Saponin-Derived Pentasaccharide from Spergularia ramosa

Organoboron-mediated regioselective glycosylations were employed as key steps in the total synthesis of a branched pentasaccharide from a saponin natural product. The ability to use organoboron activation to differentiate OH groups in an unprotected glycosyl acceptor, followed by substrate-controlled reactions of the obtained disaccharide, enabled a streamlining of the synthesis relative to a protective group-based approach. This study revealed a matching/mismatching effect of the relative configuration of donor and acceptor on the efficiency of a regioselective glycosylation reaction, a problem that was solved through the development of a novel boronic acid-amine copromoter system for glycosyl acceptor activation.

Glycosynthase with broad substrate specificity-an efficient biocatalyst for the construction of oligosaccharide library

A versatile glycosynthase (TnG-E338A) with strikingly broad substrate scope has been developed from Thermus nonproteolyticus β-glycosidase (TnG) by using site-directed mutagenesis. The practical utility of this biocatalyst has been demonstrated by the facile generation of a small library containing various oligosaccharides and a steroidal glycoside (total 25 compounds) in up to 100 % isolated yield. Moreover, an array of eight gluco-oligosaccharides has been readily synthesized by the enzyme in a one-pot, parallel reaction, which highlights its potential in the combinatorial construction of a carbohydrate library that will assist glycomic and glycotherapeutic research. Significantly, the enzyme provides a means by which glycosynthase technology may be extended to combinatorial chemistry.

STEROID COMPOUND

A steroid compound of the Formula (1): [wherein R1 represents a group selected from the group consisting of H, CH3, C2H5, C3H7 and CH (CH3)2, R2 represents a group selected from NH2, NHAc and OCOR1, R3 represents a group selected from the group consisting of CH3, COOCH3 and CH2OCOR1.]

STEROID COMPOUND

A steroid compound of the Formula (1): [wherein R1 represents a group selected from the group consisting of H, CH3, C2H5, C3H7 and CH (CH3)2, R2 represents a group selected from NH2, NHAc and OCOR1, R3 represents a group selected from the group consisting of CH3, COOCH3 and CH2OCOR1.]

Total synthesis of ipomoeassin F

The first total synthesis of ipomoeassin F was carried out using a convergent approach that relied upon the use of Schmidt glycosidation technology for the coupling of two suitably protected monosaccharide fragments. After two steps, ring-closing metathes

Total synthesis and biological evaluation of the cytotoxic resin glycosides ipomoeassin A-F and analogues

A multitasking C-silylation strategy using the readily available compound 26 as a surrogate for cinnamic acid represents the key design element of a total synthesis of all known members of the ipomoeassin family of resin glyosides. This protecting group maneuver allows the unsaturated acids decorating the glucose subunit of the targets to be attached at an early phase of the synthesis, prevents their participation in the ruthenium-catalyzed ring-closing metathesis (RCM) used to form the macrocyclic ring, and protects them against reduc tion during the hydrogenation of the resulting cycloalkene over Wilkinson's catalyst. As the C-silyl group can be concomitantly removed with the O-TBS substituent using tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) in acetonitrile, no separate protecting group manipulations were necessary in the final stages, thus contributing to a favorable overall "economy of steps". In addition to the naturally occurring ipomoeassins, a small set of synthetic analogues has also been prepared by "diverted total synthesis". The cytotoxicity of these compounds was assayed with two different cancer cell lines. The recorded data confirm previous findings that the acylation- and oxygenation pattern of these amphiphilic glycoconjugates is highly correlated with their biological activity profile. Ipomoeassin F turned out to be the most promising member of the series, showing IC50 values in the low nanomolar range.

Synthesis of per-acetyl D-fucopyranosyl bromide and its use in preparation of diphyllin D-fucopyranosyl glycoside

The per-O-acetyl-d-fucosyl bromide (9) was expediently prepared for C-6 deoxygenation of d-galactose in six steps in 32.5% yield. Employing phase transfer catalysis glycosylation (PTC), d-fucopyranosyl diphyllin (4), the analog of natural diphyllin glycoside, was synthesized by using 9 as the glycosyl donor in 67.1% in two steps. The product was identified by 1H NMR, 13C NMR, and HRMS. Its abilities to inhibit the growth of cancer cells in vitro also are discussed. Copyright Taylor & Francis Group, LLC.