162284-50-6

Basic information

• Product Name: 6-O-Benzyl-2,3-di-O-acetyl-methyl-α-D-glucopyranoside
• Synonyms: 6-O-Benzyl-2,3-di-O-acetyl-methyl-α-D-glucopyranoside;Methyl 6-O-(PhenylMethyl)-α-D-glucopyranoside 2,3-Diacetate
• CAS NO: 162284-50-6
• Molecular Formula: C₁₈H₂₄O₈
• Molecular Weight: 368.37836
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 162284-50-6.mol

Chemical Properties

• Boiling Point: 483.239°C at 760 mmHg
• Flash Point: 166.802°C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.531
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: 6-O-Benzyl-2,3-di-O-acetyl-methyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-Benzyl-2,3-di-O-acetyl-methyl-α-D-glucopyranoside(162284-50-6)
• EPA Substance Registry System: 6-O-Benzyl-2,3-di-O-acetyl-methyl-α-D-glucopyranoside(162284-50-6)

Safety Data

• Hazardous Substances Data: 162284-50-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish Oil

InChI:InChI=1/C18H24O8/c1-11(19)24-16-15(21)14(10-23-9-13-7-5-4-6-8-13)26-18(22-3)17(16)25-12(2)20/h4-8,14-18,21H,9-10H2,1-3H3/t14?,15-,16+,17+,18+/m1/s1

Upstream product

• 2774-22-3 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside 
• 4141-45-1 methyl-4,6-O-benzylidene-2,3-diacetyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 617-86-7 triethylsilane 

Downstream Products

• 935679-67-7 methyl 2,3-di-O-acetyl-6-O-benzyl-4-O-levulinyl-α-D-glucopyranoside 
• 262301-21-3 methyl 2,3-di-O-acetyl-6-O-benzyl-4-iodo-α-D-galactopyranoside 
• 1334599-37-9 methyl 4,5-di-O-acetyl-3-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-galactopyranosyl-(1->4)-2,3-di-O-acetyl-6-O-benzyl-α-D-glucopyranoside 
• 1338595-80-4 C₄₂H₅₀O₁₅ 
• 1372765-22-4 methyl 3,4-di-O-acetyl-6-O-benzyl-2-O-[(1S)-phenyl-2-(2,3,5-trimethoxyphenylsulfanyl)ethyl]-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-O-benzyl-α-D-glucopyranoside 
• 20839-38-7 methyl 6-O-benzyl-α-D-glucopyranoside 

Relevant articles and documents

A selective ring opening reaction of 4,6-O-benzylidene acetals in carbohydrates using trialkylsilane derivatives

Reductive ring opening reactions of 4,6-O-benzylidene-protected carbohydrates to the corresponding benzyl ethers using trialkylsilane derivatives were examined. When Et3SiH(or PS-DES(TM))-TfOH was used, 6-O- benzyl ethers with 4-hydroxy unsubst

Phosphotungstic acid as a novel acidic catalyst for carbohydrate protection and glycosylation

This work demonstrates the utilization of phosphotungstic acid (PTA) as a novel acidic catalyst for carbohydrate reactions, such as per-O-acetylation, regioselective O-4,6 benzylidene acetal formation, regioselective O-4 ring-opening, and glycosylation. These reactions are basic and salient during the synthesis of carbohydrate-based bioactive oligomers. Phosphotungstic acid's high acidity and eco-friendly character make it a tempting alternative to corrosive homogeneous acids. The various homogenous acid catalysts were replaced by the phosphotungstic acid solely for different carbohydrate reactions. It can be widely used as a catalyst for organic reactions as it is thermally stable and easy to handle. In our work, the reactions are operated smoothly under ambient conditions; the temperature varies from 0 °C to room temperature. Good to excellent yields were obtained in all four kinds of reactions.

The 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Group: A Novel Protecting Group in Carbohydrate Chemistry

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group was introduced to synthetic carbohydrate chemistry as a protecting group (PG) for the first time. Benefiting from a unique chemical structure and novel deprotection conditions, the DMNPA group can be cleaved rapidly and mutually orthogonal to other PGs. Orchestrated application of the DMNPA group with other PGs led to the highly efficient synthesis of the glycan of thornasterside A.

Method for preparing and removing saccharide hydroxyl protecting group dimethyl phenylacetyl DMNA

The invention relates to a method for preparing and removing saccharide hydroxyl protecting group dimethyl phenylacetyl DMNA. The method comprises the following steps: (1) efficiently introducing saccharide hydroxyl protecting group dimethyl phenylacetyl into saccharide hydroxyl; and (2) efficiently removing a hydroxyl protecting group shown in the description. The method is environmentally friendly and has the advantages that the advantages that the preparation is simple, the introduction is efficient, the operation is easy, the removal is efficient, and the application range is wide; and furthermore, a protecting group has very good stereoselectivity when being used for protecting 2-hydroxyl of a glycosyl donor, so that the development and application of the protecting group are promoted.

HClO4-silica-catalysed regioselective opening of benzylidene acetals and its application towards regioselective HO-4 glycosylation of benzylidene acetals in one-pot

Here we report a high-yielding method for the regioselective reductive ring opening of 4,6-O-benzylidene acetals of hexapyranosides using inexpensive and robust HClO4-SiO2 as the acidic catalyst and triethylsilane as the hydride dono

Cyanuric chloride/sodium borohydride: A new reagent combination for reductive opening of 4,6-benzylidene acetals of carbohydrates to primary alcohols

In the first such example, NaBH4 in combination with cyanuric chloride (TCT) has been used to obtain 6-hydroxy-4-benzyl ether derivatives from 4,6-benzylidene acetals of carbohydrates. The nature of hydride donor determines the regioselectivity

2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks

Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.

TMDS as a dual-purpose reductant in the regioselective ring cleavage of hexopyranosyl acetals to ethers

1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)2 or AlCl3 to afford the corresponding prim

Iodine-sodium cyanoborohydride-mediated reductive ring opening of 4,6-O-benzylidene acetals of hexopyranosides

A quick, efficient and convenient method for the regiospecific reductive ring opening of 4,6-O-benzylidene acetals of O-/S-alkyl/aryl glycosides of mono- and disaccharides, leading to the exclusive formation of the corresponding 6-O-benzyl ethers, using s

Regioselective reductive ring opening of benzylidene acetals using triethylsilane and iodine

Novel reaction conditions have been developed for the regioselective reductive ring opening of benzylidene acetals in carbohydrate derivatives using triethylsilane and molecular iodine. The reaction is fast, compatible with most of the functional groups e