3150-15-0

Basic information

• Product Name: METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE
• Synonyms: METHYL-2,3-ANHYDRO-4,6-O-BENZYLIDENE-A-D-ALLOPYRANOSIDE;METHYL-2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSE;METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE;methyl-2-3-anhydro-4-6-O-benzylidene*A-D-allopyra;methyl 2,3-anhydro-4,6-O-(benzylidene)-alpha-allo-D-pyranoside;METHYL-2-3-ANHYDRO-4-6-O-BENZYLIDENE*A-D -ALLOPYRANO;Methyl2,3-anhydro-4,6-O-benzylidene-a-D-allopyranose;1-O-Methyl-2,3-anhydro-4-O,6-O-(phenylmethylene)-α-D-allo-hexopyranose
• CAS NO: 3150-15-0
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.27
• EINECS: 221-582-4
• Product Categories: Sugars, Carbohydrates & Glucosides;Carbohydrates;Carbohydrates A to;Carbohydrates M-OBiochemicals and Reagents;Monosaccharide
• Mol File: 3150-15-0.mol
• Article Data: 35

Chemical Properties

• Melting Point: 201-202℃
• Boiling Point: 391.011 °C at 760 mmHg
• Flash Point: 165.408 °C
• Appearance: /
• Density: 1.322 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE(3150-15-0)
• EPA Substance Registry System: METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE(3150-15-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3150-15-0(Hazardous Substances Data)

Usage

General Description

Methyl 2,3-anhydro-4,6-O-benzylidene-alpha-D-allopyranoside is a chemical compound that is a derivative of the sugar allose. It is commonly used in organic synthesis and carbohydrate chemistry as a building block for creating more complex molecules. METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-ALPHA-D-ALLOPYRANOSIDE is often used in the development of pharmaceuticals, as well as in the production of natural products and flavors. Its unique structure and reactivity make it a valuable tool for creating a wide range of compounds with diverse biological and chemical properties.

InChI:InChI=1/C14H16O5/c1-15-14-12-11(18-12)10-9(17-14)7-16-13(19-10)8-5-3-2-4-6-8/h2-6,9-14H,7H2,1H3/t9-,10-,11-,12-,13?,14+/m1/s1

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 70774-92-4 methyl 4,6-O-benzylidene-2-O-p-toluenesulphonyl-α-D-glucopyranoside 
• 28538-15-0 methyl-[O²-benzoyl-O⁴,O⁶-((R)-benzylidene)-O³-methanesulfonyl-α-D-altropyranoside] 
• 65530-21-4 methyl 4,6-O-benzylidene-2,3-di-O-methanesulfonyl-α-D-glucopyranoside 
• 86420-67-9 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2-O-p-toluenesulfonate 
• 86420-66-8 methyl 4,6-O-benzylidene-α-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 71-43-2 benzene 
• 1385089-91-7 methyl 4,6-O-benzylidene-2,3-O-dimethanesulfonyl-α-D-galactopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 6748-86-3 methyl 4,6-O-benzylidene-β-D-galactopyranoside 2,3-di-O-p-toluenesulfonate 
• 107-18-6 allyl alcohol 
• 18423-93-3 Methyl-4,6-O-benzyliden-O-(ethoxycarbonyl)-α-D-glucopyranosid 

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 
• 74560-56-8 methyl 4,6-O-(S)-benzylidene-α-D-idopyranoside 
• 74560-63-7 methyl 4,6-O-(S)-benzylidene-3-methyl-α-D-idopyranoside 
• 2484-81-3 methyl-[O²-acetyl-3-acetylamino-O⁴,O⁶-((S)-benzylidene)-3-deoxy-α-D-idopyranoside] 
• 287191-51-9 methyl 4,6-O-benzylidene-β-D-idopyranoside 
• 6752-76-7 methyl 4,6-O-benzylidene-2-O-methyl-β-D-idopyranoside 

Relevant articles and documents

2-Diphenylarsino-, 2-diphenylphosphinyl-, and 2-triphenylstannyl-derivatives of methyl 4,6-O-benzylidene-2-deoxy-α-D-altropyranoside. Crystal structure of the phosphinyl derivative

Reaction of methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (3) with PhnMLi gives methyl 4,6-O-benzylidene-2-deoxy-2-M-α-D-altropyranoside (4; M=Ph2As, Ph2P or Ph3Sn).Compound (4, M=Ph2P) is readily oxidised in air to the phosphinyl derivative (4, M=Ph2P(O)).Characterisation of (4, M=Ph2As, Ph2P(O), or Ph3Sn) was achieved by NMR spectroscopy, including solid state NMR spectroscopy, for (4, M=Ph2As) and (4, M=Ph3Sn), and by X-ray crystallography for .In the solid state both the benzylidene and pyranose rings in , adopt chair conformations.The pentavalent phosphorus atom has a distorted tetrahedral geometry with C-P-C valency angles in the narrow range from 105.7(3) to 106.0(3) deg and the C-P-O valency angles ranging from 111.3(3) to 115.6(2) deg; the P-Caryl bond lengths are 1.808(5) and 1.815(6) Anagstroem, while the P-Calkyl bond length is slightly larger, being 1.829(6) Angstroem.Intermolecular H-bonding, involving HO and O(P) centres, links the molecules in the crystal.Keywords: Tin; Phosphorus; Arsinic; Pyranosides; Crystal structure

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.

SACCHARIDE CONJUGATES

This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.

AN EFFICIENT AND SCALABLE PROCESS FOR THE MANUFACTURE OF FONDAPARINUX SODIUM

The present invention relates to a process for the synthesis of the Factor Xa anticoagulent Fondaparinux and related compounds. The invention relates, in addition, to efficient and scalable processes for the synthesis of various intermediates useful in the synthesis of Fondaparinux and related compounds.