18465-50-4

Basic information

• Product Name: 4,6-O-Ethylidene-D-glucopyranose
• Synonyms: 4,6-O-Ethylidene-D-glucopyranoside;(1R,2S,3R,6R)-9-methyl-5,8,10-trioxabicyclo[4.4.0]decane-2,3,4-triol;4-O,6-O-Ethylidene-β-D-glucopyranose;4,6-O-Ethylidene-D-glucopyranose
• CAS NO: 18465-50-4
• Molecular Formula: C₈H₁₄O₆
• Molecular Weight: 206.19
• Mol File: 18465-50-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 386.6 °C at 760 mmHg
• Flash Point: 187.6 °C
• Appearance: /
• Density: 1.446g/cm³
• Vapor Pressure: 1.43E-07mmHg at 25°C
• Refractive Index: 1.538
• CAS DataBase Reference: 4,6-O-Ethylidene-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-O-Ethylidene-D-glucopyranose(18465-50-4)
• EPA Substance Registry System: 4,6-O-Ethylidene-D-glucopyranose(18465-50-4)

Safety Data

• Hazardous Substances Data: 18465-50-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H14O6/c1-3-12-2-4-7(13-3)5(9)6(10)8(11)14-4/h3-11H,2H2,1H3/t3?,4-,5-,6-,7-,8?/m1/s1

Upstream product

• 50-99-7 D-glucose 
• 123-63-7 paracetaldehyde 
• 2280-44-6 D-Glucose 
• 105453-29-0 1,2,3-tri-O-acetyl-4,6-O-ethylidene-β-D-glucopyranose 
• 27994-30-5 4,6-O-ethylidene-1,2,3-tri-O-acetyl-β-glucopyranose 

Downstream Products

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 901783-93-5 2,4-O-ethylidene-aldehydo-D-erythrose 
• 70377-89-8 (1'R)-(-)-2,4-O-ethylidene-D-erythrose 
• 906364-81-6 2,4-O-Ethyliden-D-erythrit 
• 70369-46-9 (2R,4S,5R)-4-hydroxymethyl-2-methyl-1,3-dioxan-5-ol 

Relevant articles and documents

A new route for preparation of 2-deoxy-D-ribofuranose phospho sugar

The addition reaction of dimethyl phosphonate to (2R,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,3-dioxan-5-one (11a), followed by dehydroxylation, provided 1-O-(tert-butyldimethylsilyl)-3-deoxy-3-dimethoxy-phosphinoyl-2,4-O-ethylidene-d-erythritol (13a). Elongation of carbon skeleton of the d-erythrose (14) derived from 13a and then acidic methanolysis gave a mixture of methyl 2,4-dideoxy-4-dimethoxyphosphinoyl-α,β-d-erythro-pentopyranosides (7), which was led to 2-deoxy-D-ribofuranose phospho sugar (4) in an appreciably improved total yield compared with the procedures via previously reported route.

β-lactams from D-erythrose-derived imines: A convenient synthesis of 2,3-diamino-2,3-dideoxy-d-mannonic-acid derivatives

The D-manno-configured N-anisylated β-lactam 40, the β-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from D-glucose in 8-10 steps, respectively. None of these compounds exhibited a significant inhibitory activity in vitro against the sialidases of Vibrio cholerae, Salmonella typhimurium, Influenza A (N9), and Influenza B virus. Cycloaddition of the in situ generated imines derived from the D-erythroses 6, 16, and 17 with the ketene from mesyloxyacetyl chloride (20) gave the 2-mesyloxy-D-hexono-1,3-lactams 25, 27a/b, 28a/b/c, and 29 in 23, 69, 57, and 90% yield, respectively (Scheme 3). Transformation of 27a/b and 29 (> 85%) to the corresponding azides, followed by oxidative N-deprotection, gave 30a/b (45%) and 34 (80%). Subsequent alkylation of the ring N-atom in 31a with benzyl bromoacetate and dibenzyl (triflyloxymethyl)phosphonate 46 gave the carboxylate 41 (77%) and the phosphonate 47 (55%; Schemes 4 and 5). Hydrogenolysis of 41 gave the β- lactam amino acid 43, besides its hydrolysis product 44. Reductive N- acylation of the azido group in 41 (93%), followed by hydrogenolytic debenzylation, yielded the 2-trifluoroacetamido N-(carboxymethyl)-β-lactam 4 (56%). Similarly, 47 gave the 2-trifluoroacetamide 48 (89%), and hence, the 2-amino-N-(phosphonoylmethyl)-β-lactams 49 (40%) and 50, resulting from deacylation of 49 (14%). Aminolysis and carbamoylation of the protected β- lactams 31a and 35 led to the 2,3-diamino-2,3-dideoxy-D-mannonamides 51 and 53, respectively (Scheme 6).

Regioselective heterogeneous O-deacylation of polyacylated sugars

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