3150-16-1

Basic information

• Product Name: Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside
• Synonyms: .alpha.-D-Mannopyranoside, methyl 2,3-anhydro-4,6-o-(phenylmethylene)-;Mannopyranoside, methyl 2,3-anhydro-4,6-o-benzylidene-, .alpha.-D-;Nsc41445;Methyl 2,3-anhydro-4,6-benzylidene-alpha-D-mannopyranoside
• CAS NO: 3150-16-1
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.275
• Mol File: 3150-16-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 146-147℃
• Boiling Point: 391°Cat760mmHg
• Flash Point: 165.4°C
• Appearance: white powder
• Density: 1.32±0.1 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside(3150-16-1)
• EPA Substance Registry System: Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside(3150-16-1)

Safety Data

• Hazardous Substances Data: 3150-16-1(Hazardous Substances Data)

Usage

Description

Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is a chemical compound that belongs to the family of mannopyranosides. It is a derivative of alpha-D-mannopyranoside, containing a methyl group and a benzylidene ring. Its unique chemical structure makes it a valuable component for the synthesis of complex carbohydrates and the development of novel pharmaceuticals.

Uses

Used in Carbohydrate Chemistry:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a key intermediate in carbohydrate chemistry for the synthesis of complex carbohydrates. Its unique structure allows for the formation of various glycosidic linkages, making it a valuable component in the development of novel carbohydrate-based compounds.
Used in Pharmaceutical Development:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a building block in the development of novel pharmaceuticals. Its potential applications in glycosylation reactions and the synthesis of complex carbohydrates make it a promising candidate for the creation of new drug molecules with improved therapeutic properties.
Used in Study of Carbohydrate-Protein Interactions:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a research tool for studying carbohydrate-protein interactions. Its unique structure allows for the investigation of how carbohydrates interact with proteins, which can provide insights into the development of carbohydrate-based materials for various technical applications.
Used in Design of Carbohydrate-Based Materials:
Methyl2,3-Anhydro-4,6-O-benzylidene-alpha-D-mannopyranoside is used as a component in the design of carbohydrate-based materials for various technical applications. Its properties and unique structure make it a valuable building block for the development of new materials with specific properties and functions.

Upstream product

• 124-41-4 sodium methylate 
• 28538-15-0 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-methanesulfonyl-α-D-altropyranoside] 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 18031-56-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-trifluoroacetyl-α-D-glucopyranoside] 
• 2647-10-1 methyl-[O⁴,O⁶-((R)-benzylidene)-O²,O³-bis-trifluoroacetyl-α-D-glucopyranoside] 
• 33535-04-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 86420-66-8 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 67-56-1 methanol 
• 71-43-2 benzene 
• 64552-06-3 methyl 4,6-O-benzylidene-α-D-galactopyranoside 
• 86420-71-5 methyl 3-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside 
• 86470-08-8 methyl 4,6-O-benzylidene-β-D-galactopyranoside 3-O-p-toluenesulfonate 
• 1824-94-8 methyl beta-D-galactopyranoside 

Downstream Products

• 497180-22-0 methyl-[O⁴,O⁶-((R)-benzylidene)-3-iodo-3-deoxy-α-D-altropyranoside] 
• 626200-80-4 methyl 4,6-O-benzylidene-3-deoxy-3-C-ethyl-α-D-altropyranoside 
• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 71184-15-1 methyl-3-deoxyamino-4,6-dioxabenzylidene-α-D-altropyranose 
• 6198-74-9 methyl (R)-3-deoxy-α-D-arabinohexopyranose 
• 72904-78-0 methyl 3-deoxy-4,6-O-phenylmethylene-α-D-arabinohexopyranoside 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 30571-48-3 methyl-[O⁴,O⁶-((R)-benzylidene)-3-bromo-3-deoxy-α-D-altropyranoside] 
• 74410-53-0 Methyl 4,6-O-benzylidene-3-O-methyl-α-D-altropyranoside 
• 131529-46-9 methyl 4,6-O-benzylidene-3-deoxy-3-C-(2-methylprop-2-enyl)-α-D-altroside 
• 131613-80-4 methyl 4,6-O-benzylidene-3-chloro-3-deoxy-α-D-altroside 
• 131529-45-8 methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside 
• 138638-68-3 Methyl 4,6-O-benzylidene-2-deoxy-2-phenylselenyl-α-D-glucopyranoside 
• 138638-64-9 Methyl 4,6-O-benzylidene-3-deoxy-3-phenylselenyl-α-D-altropyranoside 

Relevant articles and documents

A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. The stereochemical outcome of the new C–S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biological properties.

SUGAR-LINKER-DRUG CONJUGATES

The present disclosure relates to sugar-linker-drug conjugates, of the formula [A-B-]n-L-D, wherein A is a saccharide; B is a spacer, n is an integer selected from 1 to 3; L is a linker group and D is a drug having a chemically reactive functional group selected from the group consisting of a primary or secondary amine, hydroxyl, sulfhydryl, carboxyl, aldehyde and ketone. Pharmaceutical compositions comprising the conjugates and methods of using thern are also provided.

Synthesis of ribo-hexopyranoside- and altrose-based azacrown ethers and their application in an asymmetric Michael addition

The synthesis of four new ribo-hexopyranoside-based chiral lariat ethers of monoaza-15-crown-5 type and two altropyranoside-based crown ethers were elaborated. Our syntheses utilized the regioselective ring opening of the oxiran moiety of the 2,3-anhydro sugars by nucleophilic reagents to afford the key intermediates. The reaction of methyl-2,3-anhydro-4,6-O-benzylidene-α-d- mannopyranoside with ethanolamine is especially of interest to afford a 3-substituted altropyranoside. One of the ribo-hexopyranoside-based lariat ethers with a 4-methoxyphenyl substituent induced an enantioselectivity of 80% when used as catalyst in the Michael addition of diethyl acetamidomalonate to trans-β-nitrostyrene under phase transfer catalytic conditions.