13224-99-2

Basic information

• Product Name: 4,6-O-Ethylidene-alpha-D-glucose
• Synonyms: (2R,3R)-2,3-dihydroxy-3-((4R,5R)-5-hydroxy-2-methyl-1,3-dioxan-4-yl)propanal;(4aR,6S,7R,8R,8aS)-2-Methylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol;(4AR,7R,8R,8aS)-2-Methylhexahydropyrano-[3,2-d][1,3]dioxine-6,7,8-triol;NSC 89726;-D-glucopyranose;4,6-O-Ethylidene-α4,6-O-ETHYLIDENE-A-D-GLUCOSE;4,6-O-ETHYLIDENE-ALPHA-D-GLUCOPYRANOSE
• CAS NO: 13224-99-2
• Molecular Formula: C₈H₁₄O₆
• Molecular Weight: 206.19
• EINECS: 236-496-2
• Product Categories: Sugars;Carbohydrate Synthesis;Specialty Synthesis;Monosaccharides;Sugars, Carbohydrates & Glucosides;Biochemistry;Glucose;O-Substituted Sugars
• Mol File: 13224-99-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 168-170 °C(lit.)
• Boiling Point: 386.571ºC at 760 mmHg
• Flash Point: >110°(230°F)
• Appearance: White to Off-white/Powder
• Density: 1.447g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.539
• Solubility: Ethanol, Water
• PKA: 12.01±0.70(Predicted)
• Water Solubility: almost transparency
• CAS DataBase Reference: 4,6-O-Ethylidene-alpha-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-O-Ethylidene-alpha-D-glucose(13224-99-2)
• EPA Substance Registry System: 4,6-O-Ethylidene-alpha-D-glucose(13224-99-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 13224-99-2(Hazardous Substances Data)

Usage

Description

4,6-O-Ethylidene-alpha-D-glucose is a modified carbohydrate molecule derived from alpha-D-glucose, featuring an ethylidene group at the 4,6 positions. This modification enhances its stability and reactivity, making it a valuable intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
4,6-O-Ethylidene-alpha-D-glucose is used as an intermediate in the synthesis of α-Etoposide (E933745), a potent cytotoxic agent and anticancer drug. It belongs to the drug class of topoisomerase inhibitors, which play a crucial role in the treatment of various malignancies by inhibiting the activity of topoisomerases, essential enzymes in DNA replication and transcription.
Additionally, 4,6-O-Ethylidene-alpha-D-glucose serves as an antineoplastic drug, contributing to the development of novel therapeutic agents that target cancer cells and inhibit their growth and proliferation. Its unique structure and properties make it a promising candidate for the advancement of cancer treatment strategies.

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

• 2280-44-6 D-Glucose 
• 123-63-7 paracetaldehyde 
• 50-99-7 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

• 70369-46-9 (2R,4S,5R)-4-hydroxymethyl-2-methyl-1,3-dioxan-5-ol 
• 1613708-53-4 C₁₇H₂₂N₂O₇ 
• 1613708-51-2 C₂₅H₃₆N₂O₁₂ 
• 1360882-53-6 2,6-bis-(4(4,6-O-ethylidene-β-D-glucopyranosyl-amino)phenyl)-4-(3,4,5-tri-O-octyl-phenyl)pyridine 
• 1360882-51-4 2,6-bis-(4(4,6-O-ethylidene-β-D-glucopyranosyl-amino)phenyl)-4-(3,4-di-O-octyl-phenyl)pyridine 
• 1360882-49-0 2,6-bis-(4(4,6-O-ethylidene-β-D-glucopyranosyl-amino)phenyl)-4-(4-O-octyl-phenyl)pyridine 

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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