13121-61-4

Basic information

• Product Name: 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol
• Synonyms: 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol;1,5-Anhydro-D-Mannitol Tetraacetate;NSC 231899
• CAS NO: 13121-61-4
• Molecular Formula: C₁₄H₂₀O₉
• Molecular Weight: 332.3032
• Product Categories: Carbohydrates & Derivatives
• Mol File: 13121-61-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 104-105 °C
• Boiling Point: 383.3°Cat760mmHg
• Flash Point: 166°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 4.45E-06mmHg at 25°C
• Refractive Index: 1.475
• Solubility: Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol(13121-61-4)
• EPA Substance Registry System: 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-D-mannitol(13121-61-4)

Safety Data

• Hazardous Substances Data: 13121-61-4(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Oil

Uses

Protected mannitol derivative

InChI:InChI=1/C14H20O9/c1-7(15)19-5-11-13(22-9(3)17)14(23-10(4)18)12(6-20-11)21-8(2)16/h11-14H,5-6H2,1-4H3

Upstream product

• 211801-79-5 4-methylphenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 73804-33-8 ethyl 1-thio-β-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 69-65-8 mannitol 
• 3458-28-4 D-Mannose 
• 88567-49-1 6-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 88567-51-5 methyl [(2R,3R,4S,5R)-3,4,5-tribenzyloxy-6-oxo-tetrahydropyran-2-yl]acetate 
• 4356-77-8 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-glucopyranose 
• 82682-67-5 (2R,3R,4R,5R)-3,4,5-Tris-trimethylsilanyloxy-2-trimethylsilanyloxymethyl-tetrahydro-pyran 
• 1769-06-8 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-mannopyranoside 
• 4851-64-3 phosphoric acid diethyl ester vinyl ester 

Downstream Products

• 536745-69-4 (2R,4aR,8aS)-8-Methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 539823-59-1 O²,O³;O⁴,O⁶-dibenzyliden-1,5-anhydro-mannitol 
• 63554-21-2 (2R,4aR,8aR)-2-Phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 
• 492-93-3 1,5-anhydro-D-mannitol 

Relevant articles and documents

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Reduction of glycosyl bromides to anhydroalditols by titanocene borohydride

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Additive-controlled synthesis of 1- and 2-dexoysugars from thioglycosides

Two photoreactions for the synthesis of 1- and 2-deoxysugars from thioglycosides were developed. In the presence of Hantzsch ester as an additive, a wide range of 1-deoxysugars were synthesized in moderate to excellent yields under irradiation with UV light without an exogenous photosensitizer. On the other hand, the utilization of 2,4,6-tri-tert-butylpyrimidine (TTBP) as the additive furnished a variety of 2-deoxysugars as the main products from their corresponding thioglycosides. The reported methodology has a broad substrate scope and high functional group tolerance and is scalable to gram-scale reaction.

Synthesis of octahydropyrano[3,2-b]pyrrole-2-carboxylic acid derivatives from d-mannose

Bicyclic amino acids are useful building blocks in synthesizing biologically active molecules and peptidomimetics. 2-Carboxy-6-hydroxyloctahydroindole (Choi) is a novel bicyclic amino acid found in the marine natural products aeruginosins. Many compounds in the aeruginosin family exhibit inhibition activities toward serine proteases including thrombin and trypsin. The unique Choi structure is the common feature of this family of oligopeptides and this motif is important for their observed biological activities. To better understand the influence of the stereochemistry of the Choi core structure on the inhibition activities, we have previously synthesized ring-oxygenated variants from glucose. The preparation of octahydro-pyrano[3,2-b]pyrrole 2-carboxylic acids from d-mannose is reported here. These novel bicyclic amino acids can be used in the preparation of aeruginosin analogs, as well as conformationally constrained peptidomimetics or other biologically active molecules.

Towards α- or β-D-C-glycosyl compounds by tin-catalyzed addition of glycosyl radicals to acrylonitrile and vinylphosphonate, and flexible reduction of tetra-O-acetyl-α-D-glucopyranosyl bromide with cyanoborohydride

Photo-induced radical addition of acetylated α-D-glucopyranosyl bromide (1) to acrylonitrile or diethyl vinylphosphonate, in the presence of catalytic amounts of tri-n-butyltin chloride and sodium (or tetra-n-butylammonium) cyanoborohydride in excess, all