4148-71-4

Basic information

• Product Name: METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE
• Synonyms: METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE;Methyl 2,3:4,6-Di-O-benzylidene-α-D-mannopryanoside;Methyl 2,3:4,6-Di-O-benzylidene-alpha-D-mannopyranoside;Methyl 2,3:4,6-Bis-O-(phenylMethylene)-;Methyl 2,3:4,6-Di-O-benzylidene-α-D-Mannopyranoside;(3aS,4S,5aR,9aR,9bS)-4-methoxy-2,8-diphenyl-3a,4,5a,6,9a,9b-hexahydro-[1,3]dioxolo[2,3]pyrano[2,4-d][1,3]dioxine
• CAS NO: 4148-71-4
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.4
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 4148-71-4.mol

Chemical Properties

• Melting Point: 182-184°C
• Boiling Point: 514.7°Cat760mmHg
• Flash Point: 212.9°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 3.4E-10mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• CAS DataBase Reference: METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE(4148-71-4)
• EPA Substance Registry System: METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE(4148-71-4)

Safety Data

• Hazardous Substances Data: 4148-71-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE is used as a synthetic intermediate for the production of (+)-ajmalicine, a compound with potential applications in the development of pharmaceuticals. This intermediate plays a crucial role in the synthesis of various organic compounds that can be used for medicinal purposes.
Used in Carbohydrate Chemistry:
METHYL-2,3:4,6-DI-O-BENZYLIDINE-D-MANNOPYRANOSIDE is used as a synthetic intermediate in carbohydrate chemistry, where it aids in the synthesis of complex carbohydrate structures. These structures can be employed in various applications, such as the development of new drugs, the study of carbohydrate interactions, and the creation of novel materials with specific properties.

InChI:InChI=1/C21H22O6/c1-22-21-18-17(26-20(27-18)14-10-6-3-7-11-14)16-15(24-21)12-23-19(25-16)13-8-4-2-5-9-13/h2-11,15-21H,12H2,1H3

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 100-52-7 benzaldehyde 
• 22277-65-2 Methyl mannoside 
• 100-39-0 benzyl bromide 
• 108-24-7 acetic anhydride 

Downstream Products

• 4148-58-7 (4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 86342-20-3 methyl 2,6-di-O-benzyl-β-D-mannopyranoside 
• 86342-19-0 methyl 2,4-di-O-benzyl-β-D-mannopyranoside 
• 15038-71-8 methyl 2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 57783-73-0 methyl 3,4-di-O-benzyl-β-D-mannopyranoside 
• 2774-19-8 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside 
• 95015-49-9 methyl 3,4-di-O-benzoyl-2,6-di-O-benzyl-α-D-mannopyranoside 
• 88110-50-3 methyl 2,3-di-O-benzyl-4-O-methyl-6-O-trityl-α-D-mannopyranoside 
• 88110-52-5 methyl (methyl 2,3-di-O-benzyl-4-O-methyl-α-D-mannopyranosid)uronate 
• 88110-49-0 methyl (methyl 3,4-di-O-benzyl-2-O-methyl-α-D-mannopyranosid)uronate 
• 88110-51-4 methyl 2,3-di-O-benzyl-4-O-methyl-α-D-mannopyranoside 
• 83238-30-6 methyl 3,4-di-O-benzyl-2-O-methyl-α-D-mannopyranoside 
• 64605-18-1 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-methyl-α-D-mannopyranoside 
• 51842-18-3 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 

Relevant articles and documents

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

Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks

Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars.

Selective 4,6-O-benzylidene formation of methyl α-d-mannopyranoside using 2,6-dimethylbenzaldehyde

While methyl α-d-glucopyranosides and α-d-galactopyranosides selectively form 4,6-O-benzylidenes when reacted with excess benzaldehyde in the presence of acid catalyst methyl α-d-mannopyranosides does not exhibit the same selectivity because of the cis-ar

Carbohydrate Phosphinites as Practical Ligands in Asymmetric Catalysis: Electronic Effects and Dependence of Backbone Chirality in Rh-Catalyzed Asymmetric Hydrogenations. Synthesis of R- or S-Amino Acids Using Natural Sugars as Ligand Precursors

Vicinal diarylphosphinites derived from carbohydrates are excellent ligands for the Rh(I)-catalyzed enantioselective asymmetric hydrogenation of dehydroamino acid derivatives, producing the highest enantioselectivity of any ligands directly prepared from natural products. The enantioselectivity can be enhanced by the appropriate choice of substituents on the aromatic rings of the phosphinites. For example, the use of phosphinites with electron-donating bis(3,5-dimethylphenyl) groups on phosphorus provides ee's up to 99% for a wide range of amino acids including some with easily removable N-protecting groups. Electron-withdrawing aryl substituents, on the other hand, decrease the enantioselectivity. Sense of chiral induction in the amino acid product depends on the relative juxtaposition of the vicinal diphosphinites on a given sugar backbone. When readily available D-glucopyranosides are used as the starting sugars, 2,3-phosphinites give the S-amino acids and 3,4-phosphinites give the R-amino acids. In the case of aromatic and heteroaromatic amino acids, enantioselectivities > 95% are consistently obtained. Practical considerations such as the ease of ligand synthesis, rates of reactions, catalyst turnover, and scope and limitations in terms of substrates are discussed. A possible explanation for the enhancement of enantioselectivity by electron-rich phosphinites is offered.

CHEMO-, STEREO- AND REGIOSELECTIVE HYDROGENOLYSIS OF CARBOHYDRATE BENZYLIDENE ACETALS. SYNTHESIS OF BENZYL ETHERS OF BENZYL α-D-, METHYL β-D-MANNOPYRANOSIDES AND BENZYL α-D-RHAMNOPYRANOSIDE BY RING CLEAVAGE OF BENZYLIDENE DERIVATIVES WITH THE LiAlH4-AlCl3

Treatment of benzyl α-(1) and methyl β-D-mannopyranoside (2) with α,α-dimethoxytoluene gave the exo and endo isomers (3,5 and 4,6) of the dibenzylidene derivatives of 1 and 2.Hydrogenolysis of the exo isomers (3 and 5) with a molar equivalent of AlH2Cl ga

Synthesis of daunosamine hydrochloride from a D-mannose starting material

A method for synthesizing daunosamine hydrochloride from methyl α-D-mannopyranoside. The major features of the preparative route involve the formation of a 2-deoxy-3-keto intermediate, whose oxime is reduced with high stereoselectivity to the D-ribo-3-ami