74247-81-7

Basic information

• Product Name: METHYL-A-D-6-O-T-BUTYLDIMETHYL-MANNOPYRANOSIDE
• Synonyms: METHYL-A-D-6-O-T-BUTYLDIMETHYL-MANNOPYRANOSIDE
• CAS NO: 74247-81-7
• Molecular Formula: C₁₃H₂₈O₆Si
• Molecular Weight: 308.44
• Mol File: 74247-81-7.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 375.4°C at 760 mmHg
• Flash Point: 180.8°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 3.59E-07mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: METHYL-A-D-6-O-T-BUTYLDIMETHYL-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-A-D-6-O-T-BUTYLDIMETHYL-MANNOPYRANOSIDE(74247-81-7)
• EPA Substance Registry System: METHYL-A-D-6-O-T-BUTYLDIMETHYL-MANNOPYRANOSIDE(74247-81-7)

Safety Data

• Hazardous Substances Data: 74247-81-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H28O6Si/c1-13(2,3)20(5,6)18-7-8-9(14)10(15)11(16)12(17-4)19-8/h8-12,14-16H,7H2,1-6H3/t8-,9-,10+,11+,12+/m1/s1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 82112-21-8 N,O-bis(tertbutyldimethylsilyl)acetamide 
• 29681-57-0 tert-butyldimethylsilane 
• 143422-89-3 (2-methylallyl)tertiobutyl-dimethylsilane 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 79293-84-8 N-(tert-butyldimethylsilyl)phthalimide 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 206186-94-9 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 

Downstream Products

• 126502-43-0 Methyl 6-O-<(1,1-dimethylethyl)dimethylsilyl>-3-O-(phenylmethyl)-β-D-galactopyranoside 
• 128142-70-1 methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 853879-39-7 benzoic acid 3,5-dibenzoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester 
• 174618-10-1 methyl 2,3,4-tri-O-acetyl-6-(tert-butyldimethylsiloxy)-β-D-galactopyranoside 
• 206186-94-9 methyl 2,3,4-tri-O-benzyl-6-O-tert-butyldimethylsilyl-α-D-mannopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 63734-11-2 acetic acid 3,5-diacetoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester 
• 914799-09-0 methyl 2,3,4-tri-O-acetate-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 
• 945033-05-6 C₃₅H₃₇O₈N 
• 945033-06-7 C₃₆H₃₇O₉N 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 220853-26-9 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-diethoxyphosphinoylmethylene-α-D-mannopyranoside 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 

Relevant articles and documents

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Catalytic Site-Selective Carbamoylation of Pyranosides

Carbamate-bearing carbohydrates contribute to the pharmacological properties of various natural glycosides. The catalytic site-selective carbamoylation of minimally protected pyranosides was achieved for the first time to bypass protection/deprotection sequences. 1-Carbamoylimidazoles were used as the carbamoylation reagents to circumvent the harmful and unstable phosgene and isocyanates. This borinic acid catalyzed transformation granted an expedient access to the tumor cell-binding carbamoylmannoside moiety of bleomycins and analogs in yields of 56% to 89%.

Addressing the biochemical foundations of a glucose-based "trojan horse"-strategy to boron neutron capture therapy: From chemical synthesis to in vitro assessment

Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital neutron accelerators which are expected to revolutionize patient treatments. There is an urgent need for improved boron delivery agents, and herein we have focused on studying the biochemical foundations upon which a successful GLUT1-targeting strategy to BNCT could be based. By combining synthesis and molecular modeling with affinity and cytotoxicity studies, we unravel the mechanisms behind the considerable potential of appropriately designed glucoconjugates as boron delivery agents for BNCT. In addition to addressing the biochemical premises of the approach in detail, we report on a hit glucoconjugate which displays good cytocompatibility, aqueous solubility, high transporter affinity, and, crucially, an exceptional boron delivery capacity in the in vitro assessment thereby pointing toward the significant potential embedded in this approach.