14419-69-3

Basic information

• Product Name: (3-O-BENZYL-4,6-O-BENZYLIDENE) METHYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: (3-O-BENZYL-4,6-O-BENZYLIDENE) METHYL-ALPHA-D-GLUCOPYRANOSIDE;(3-o-Benzyl-4,6-benzylidene) methyl-alpha-D-glucopyranoside
• CAS NO: 14419-69-3
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.41
• Mol File: 14419-69-3.mol
• Article Data: 45

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3-O-BENZYL-4,6-O-BENZYLIDENE) METHYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (3-O-BENZYL-4,6-O-BENZYLIDENE) METHYL-ALPHA-D-GLUCOPYRANOSIDE(14419-69-3)
• EPA Substance Registry System: (3-O-BENZYL-4,6-O-BENZYLIDENE) METHYL-ALPHA-D-GLUCOPYRANOSIDE(14419-69-3)

Safety Data

• Hazardous Substances Data: 14419-69-3(Hazardous Substances Data)

Usage

Description

(3-O-Benzyl-4,6-O-benzylidene) methyl-alpha-D-glucopyranoside is a glycoside chemical compound derived from glucose. It features a benzyl group at the 3rd carbon and a benzylidene group linking the hydroxyl groups at the 4th and 6th carbons. This unique structure and functional groups make it a valuable compound for research and development in organic synthesis and medicinal chemistry.

Uses

Used in Organic Synthesis:
(3-O-Benzyl-4,6-O-benzylidene) methyl-alpha-D-glucopyranoside is used as a building block for the synthesis of complex natural products. Its unique structure and functional groups make it a valuable compound for further research and development in the field of chemistry.
Used in Medicinal Chemistry:
(3-O-Benzyl-4,6-O-benzylidene) methyl-alpha-D-glucopyranoside is used in the development of carbohydrate-based drugs. Its potential applications in this field highlight its importance in pharmaceutical research and development.

Upstream product

• 22277-65-2 Methyl mannoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 4148-71-4 methyl exo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside 
• 93714-01-3 methyl 3-O-benzyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 100-52-7 benzaldehyde 
• 76419-48-2 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 3162-96-7 methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 
• 65877-18-1 methyl 4,6-O-benzylidene-2,3-O-(dibutyl-stannylidene)-α-D-mannopyranoside 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 73395-14-9 methyl (R,R)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-β-D-galactopyranoside 

Downstream Products

• 189240-81-1 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2',3'-epoxypropyl)-α-D-glucopyranoside 
• 65533-40-6 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-erythro-hex-2-enopyranoside 
• 329307-84-8 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)mannopyranoside 
• 329307-81-5 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)glucopyranoside 
• 329307-92-8 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-(2-2H)mannopyranoside 
• 329307-85-9 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifyl-α-D-(2-2H)mannopyranoside 
• 329307-82-6 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifyl-α-D-(2-2H)glucopyranoside 
• 1323140-37-9 methyl 3-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1323140-39-1 methyl 3-O-benzyl-6-O-(2,3,4-tri-O-benzyl-β-L-fucopyranosyl)-α-D-glucopyranoside 
• 1379442-52-0 methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 40010-11-5 methyl 3-O-benzyl-α-D-glucopyranoside 
• 40010-11-5 methyl 3-O-benzyl-β-D-galactopyranoside 
• 158799-80-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside 
• 130983-50-5 methyl 3-O-benzyl-4,6-O-benzylidene-α-D-arabino-hexopyranosid-2-ulose 

Relevant articles and documents

SnCl2-Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

Based on SnCl2-catalyzed acetalation and selective benzoylation, a one-pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2-OH/3-OH was developed. Consequently, 2-OBz or 3-OBz 4,6-O-benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species

A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond