34234-44-1

Basic information

• Product Name: METHYL 2,3,4-TRI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 2,3,4-TRI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE;Methyl2,3,6-tri-O-benzoyl-a-D-glucopyranoside;Methyl 2,3,4-Tri-O-benzoyl-α-D-glucopyranoside;Methyl 2,3,6-tri-O-benzoyl-a-D-glucopyranoside ,98%;Methyl 2,3,6-tri-O-benzoyl-α-D-glucopyranoside;Methyl 2,3,4-Tri-O-benzoyl-α(2R,3R,4S,5R,6S)-2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl tribenzoate;OTHER ORGANIC COMPOUNDS : DIBENZO[B,F][1,4]THIAZEPIN-11-(10H)-ONE (DTO)
• CAS NO: 34234-44-1
• Molecular Formula: C₂₈H₂₆O₉
• Molecular Weight: 506.5
• Product Categories: Biochemistry;Glucose;Glycosides;O-Substituted Sugars;Sugars
• Mol File: 34234-44-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: 146 °C
• Boiling Point: 658.045oC at 760 mmHg
• Flash Point: 217.175oC
• Appearance: /
• Density: 1.352g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 53.5 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: soluble in Chloroform
• CAS DataBase Reference: METHYL 2,3,4-TRI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3,4-TRI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE(34234-44-1)
• EPA Substance Registry System: METHYL 2,3,4-TRI-O-BENZOYL-ALPHA-D-GLUCOPYRANOSIDE(34234-44-1)

Safety Data

• Hazardous Substances Data: 34234-44-1(Hazardous Substances Data)

Usage

Chemical Properties

White or off-white powder

InChI:InChI=1/C28H26O9/c1-33-28-24(37-27(32)20-15-9-4-10-16-20)23(36-26(31)19-13-7-3-8-14-19)22(21(17-29)34-28)35-25(30)18-11-5-2-6-12-18/h2-16,21-24,28-29H,17H2,1H3/t21-,22-,23+,24-,28+/m1/s1

Upstream product

• 198338-59-9 methyl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside 
• 98-88-4 benzoyl chloride 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 20231-39-4 methyl 2,3,4-tri-O-benzoyl-6-O-triphenylmethyl-α-D-glucopyranoside 
• 128142-70-1 methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 120200-51-3 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 92516-59-1 methyl 6-azido-2,3,4-tri-O-benzoyl-6-deoxy-α-D-idopyranoside 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 
• 1504584-80-8 methyl 6-O-(2-((naphthalen-2-ylmethoxy)methyl)benzoyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 1504584-79-5 methyl 2,3,4-tri-O-benzoyl-6-(4-(4-naphthalen-2-ylmethoxy)butanoyl)-α-D-glucopyranoside 
• 1504584-78-4 methyl 2,3,4-tri-O-benzoyl-6-(2-((4-methoxybenzyloxy)methyl)benzoyl)-α-D-glucopyranoside 
• 1504584-77-3 methyl 2,3,4-tri-O-benzoyl-6-(4-(4-methoxybenzyloxy)butanoyl)-α-D-glucopyranoside 
• 356060-80-5 methyl 2,3,4-tri-O-benzoyl-6-triisopropylsilyl-α-D-glucopyranoside 

Downstream Products

• 4159-55-1 methyl 6-O-(β-D-glucopyranosyl)-α-D-glucopyranoside 
• 116730-81-5 Methyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 116730-77-9 methyl 6-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 165680-85-3 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 130050-83-8 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 194471-78-8 (2S,3R,4S,5R,6R)-2-methoxy-6-((((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 190515-39-0 (2S,3R,4S,5R,6R)-2-methoxy-6-((((2S,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 
• 91318-11-5 methyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 130050-83-8 methyl (2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 635321-20-9 methyl (2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 125135-28-6 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 34340-06-2 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 172364-85-1 methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 
• 149818-84-8 methyl 6-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 

Relevant articles and documents

4-(tert -Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality

Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting groups is also investigated. Due to its advantageous properties, BDMB is anticipated to function as a valuable agent for masking hydroxy groups.

Dual-participation protecting group solves the anomeric stereocontrol problems in glycosylation reactions

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.