4484-88-2

Basic information

• Product Name: [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid
• Synonyms: [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid;Trehalose 6-phosphate
• CAS NO: 4484-88-2
• Molecular Formula: C₁₂H₂₃O₁₄P
• Molecular Weight: 422.28
• Mol File: 4484-88-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 789.7°C at 760 mmHg
• Flash Point: 431.4°C
• Appearance: /
• Density: 1.89g/cm³
• Vapor Pressure: 7.99E-29mmHg at 25°C
• Refractive Index: 1.646
• CAS DataBase Reference: [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid(4484-88-2)
• EPA Substance Registry System: [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid(4484-88-2)

Safety Data

• Hazardous Substances Data: 4484-88-2(Hazardous Substances Data)

Usage

Description

[3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid is a complex organic compound characterized by its multiple hydroxyl and methoxy groups. It is a derivative of phosphonic acid, which is known for its ability to form stable complexes with metal ions. [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid's unique structure and functional groups make it a potential candidate for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
[3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid is used as a chelating agent for the stabilization of metal ions in pharmaceutical formulations. Its ability to form stable complexes with metal ions can help prevent the degradation of active pharmaceutical ingredients and improve the overall stability of the drug product.
Used in Agrochemical Industry:
In the agrochemical industry, [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid is used as a component in the synthesis of various agrochemicals, such as pesticides and fertilizers. Its chelating properties can enhance the effectiveness of these products by improving the solubility and bioavailability of essential nutrients and active ingredients.
Used in Chemical Synthesis:
[3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid is used as an intermediate in the synthesis of various complex organic compounds. Its unique structure and functional groups make it a valuable building block for the development of new molecules with potential applications in various fields, such as materials science, pharmaceuticals, and agrochemicals.
Used in Environmental Applications:
In environmental applications, [3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid can be used for the removal of heavy metal ions from contaminated water sources. Its chelating properties allow it to form stable complexes with these metal ions, facilitating their removal and reducing the environmental impact of heavy metal pollution.
Used in Material Science:
[3,4,5-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxan-2-yl]methoxyphosphonic acid can be used in the development of new materials with unique properties. Its ability to form stable complexes with metal ions can be exploited to create materials with enhanced mechanical, electrical, or optical properties, depending on the specific application.

InChI:InChI=1/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1

Synthetic route

6-O-diphenoxyphosphoryl-α,α-D-trehalose (1253891-13-2) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With platinum(IV) oxide; hydrogen; acetic acid In ethanol; water at 20℃; for 14h;	99%
With platinum(IV) oxide; hydrogen; acetic acid In ethanol; water at 20℃; under 760.051 Torr; for 5h;	94%
With hydrogen; platinum(IV) oxide; acetic acid In ethanol; water at 20℃; under 760.051 Torr; for 5h;	94%
Multi-step reaction with 2 steps 1: sodium carbonate / dichloromethane / 80 h / Reflux 2: trimethylsilyl iodide / 1,4-dioxane / 0.25 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate / 18 h / 80 °C 2: trimethylsilyl iodide / 1,4-dioxane / 0.25 h / 20 °C View Scheme

6-O-(dimethoxyphosphoryl)-D-trehalose (1274878-36-2) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With trimethylsilyl iodide In 1,4-dioxane at 20℃; for 0.25h;	87%

6-O-(dimethoxyphosphoryl)-D-trehalose (1274878-36-2) → 6-azido-trehalose (1274877-19-8) + trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Stage #1: 6-O-(dimethoxyphosphoryl)-D-trehalose With trimethylsilyl bromide In 1,4-dioxane at 20℃; for 3h; Stage #2: With water In 1,4-dioxane	A 52% B 11%

D-Glucose (2280-44-6) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With baker's yeast; sodium phosphate buffer; magnesium sulfate; 5'-Uridylic Acid at 37℃; for 6h;	11%
With baker's yeast; sodium phosphate buffer; magnesium sulfate; 5'-Uridylic Acid at 37℃; for 6h; Product distribution; effects of aeration, pH, concentration;	11%

D-Fructose (57-48-7) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With disodium hydrogenphosphate; top fermenting brewer's yeast

D-glucose (50-99-7) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With disodium hydrogenphosphate; top fermenting brewer's yeast
With sodium dihydrogenphosphate; bottom fermented brewer's yeast; water; sodium hydrogencarbonate Reagens 4: Toluol;

C33H77Cl2O12PSi7 → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With water for 0.5h; Ambient temperature; Yield given;

2,3,4,2',3',4′,6'-heptakis-O-(trimethylsilyl)-α,α-trehalose (60065-05-6) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: POCl3, N-ethylmorpholine / CH2Cl2 / Ambient temperature 2: H2O / 0.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; trichlorophosphate / 0.17 h / 20 °C 1.2: 1 h / 20 °C 1.3: Dowex 2.1: 0.75 h / 125W/365nm radiation; Aqueous phosphate buffer View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; trichlorophosphate / 0.17 h / 20 °C 1.2: 1 h / 20 °C 1.3: Dowex 2.1: 1 h / 125W/365nm radiation; Aqueous phosphate buffer View Scheme

2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose (42390-78-3) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 36 percent / methanolic K2CO3 / 0.33 h / 0 - 4 °C 2: POCl3, N-ethylmorpholine / CH2Cl2 / Ambient temperature 3: H2O / 0.5 h / Ambient temperature View Scheme

TREHALOSE (99-20-7) → 6-azido-trehalose (1274877-19-8) + trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 18 h / 20 °C 2: trimethylsilyl bromide / 1,4-dioxane / 3 h / 20 °C View Scheme

TREHALOSE (99-20-7) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 18 h / 20 °C 2: hydrogen / acetic acid; platinum(IV) oxide / ethanol; water / 5 h / 20 °C / 760.05 Torr View Scheme
Multi-step reaction with 3 steps 1: pyridine; dmap / 3 h / 20 °C 2: sodium carbonate / dichloromethane / 80 h / Reflux 3: trimethylsilyl iodide / 1,4-dioxane / 0.25 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine; dmap / 3 h / 20 °C 2: triethylamine; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate / 18 h / 80 °C 3: trimethylsilyl iodide / 1,4-dioxane / 0.25 h / 20 °C View Scheme

6-O-bis-(2-nitrobenzyloxyphosphoryl)-D-trehalose (1404341-55-4) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
for 0.5h; Product distribution / selectivity; 125W/365nm radiation; Aqueous phosphate buffer;

C47H89N2O18PSi7 → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h 2: 0.5 h / 125W/365nm radiation; Aqueous phosphate buffer View Scheme

6-O-bis-(4,5-dimethoxy-2-nitrobenzyloxyphosphoryl)-D-trehalose (1404341-58-7) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
for 1h; Product distribution / selectivity; 125W/365nm radiation; Aqueous phosphate buffer;

C51H97N2O22PSi7 → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h 2: 1 h / 125W/365nm radiation; Aqueous phosphate buffer View Scheme

6-O-bis[1-(2-nitrophenyl)ethoxyphosphoryl]-D-trehalose (1404341-61-2) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
for 0.333333h; Product distribution / selectivity; 125W/365nm radiation; Aqueous phosphate buffer;

C49H93N2O18PSi7 → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 1 h 2: 0.33 h / 125W/365nm radiation; Aqueous phosphate buffer View Scheme

6-O-(4,5-dimethoxy-2-nitrobenzyloxyphosphoryl)-D-trehalose (1404341-64-5) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
for 0.75h; Product distribution / selectivity; 125W/365nm radiation; Aqueous phosphate buffer;

α-D-glucose 6-phosphate (299-31-0, 15209-11-7, 15209-12-8, 33163-99-4, 40436-57-5, 40436-58-6, 40436-60-0, 40436-61-1) + uridine diphosphate glucose (133-89-1) → trehalose 6-phosphate (4484-88-2)

Conditions	Yield
With trehalose-6-phosphate synthase Enzymatic reaction;

trehalose 6-phosphate (4484-88-2) + aqueous sulfuric acid (0.2 n) → D-glucose (50-99-7) + D-glucose 6-phosphate (56-73-5, 3672-15-9, 6665-00-5, 82259-50-5, 89396-13-4, 92418-43-4, 136376-93-7, 136376-97-1, 136377-00-9, 136377-02-1, 136377-04-3, 136377-07-6, 136377-08-7, 136377-11-2, 136377-13-4, 136377-14-5, 136457-25-5) + phosphoric acid (86119-84-8, 7664-38-2)

Conditions	Yield
at 100℃; Rate constant; Hydrolysis;

trehalose 6-phosphate (4484-88-2) + aqueous sulfuric acid (1 n) → D-glucose (50-99-7) + D-glucose 6-phosphate (56-73-5, 3672-15-9, 6665-00-5, 82259-50-5, 89396-13-4, 92418-43-4, 136376-93-7, 136376-97-1, 136377-00-9, 136377-02-1, 136377-04-3, 136377-07-6, 136377-08-7, 136377-11-2, 136377-13-4, 136377-14-5, 136457-25-5) + phosphoric acid (86119-84-8, 7664-38-2)

Conditions	Yield
at 100℃; Rate constant; Hydrolysis;

trehalose 6-phosphate (4484-88-2) → TREHALOSE (99-20-7)

Conditions	Yield
With trehalose-6-phosphate phosphatase Enzymatic reaction;

Upstream product

• 57-48-7 D-Fructose 
• 50-99-7 D-glucose 
• 2280-44-6 D-Glucose 
• 60065-05-6 2,3,4,2',3',4′,6'-heptakis-O-(trimethylsilyl)-α,α-trehalose 
• 42390-78-3 2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose 
• 1253891-13-2 6-O-diphenoxyphosphoryl-α,α-D-trehalose 
• 99-20-7 TREHALOSE 
• 1274878-36-2 6-O-(dimethoxyphosphoryl)-D-trehalose 
• 1404341-55-4 6-O-bis-(2-nitrobenzyloxyphosphoryl)-D-trehalose 
• 1404341-58-7 6-O-bis-(4,5-dimethoxy-2-nitrobenzyloxyphosphoryl)-D-trehalose 
• 1404341-61-2 6-O-bis[1-(2-nitrophenyl)ethoxyphosphoryl]-D-trehalose 
• 1404341-64-5 6-O-(4,5-dimethoxy-2-nitrobenzyloxyphosphoryl)-D-trehalose 
• 299-31-0 α-D-glucose 6-phosphate 
• 133-89-1 uridine diphosphate glucose 

Downstream Products

• 50-99-7 D-glucose 
• 56-73-5 D-glucose 6-phosphate 
• 86119-84-8 phosphoric acid 
• 99-20-7 TREHALOSE 

Relevant articles and documents

Structures of trehalose-6-phosphate phosphatase from pathogenic fungi reveal the mechanisms of substrate recognition and catalysis

Trehalose is a disaccharide essential for the survival and virulence of pathogenic fungi. The biosynthesis of trehalose requires trehalose-6-phosphate synthase, Tps1, and trehalose-6-phosphate phosphatase, Tps2. Here, we report the structures of the N-terminal domain of Tps2 (Tps2NTD) from Candida albicans, a transition-state complex of the Tps2 C-terminal trehalose-6-phosphate phosphatase domain (Tps2PD) bound to BeF3 and trehalose, and catalytically dead Tps2PD(D24N) from Cryptococcus neoformans bound to trehalose-6-phosphate (T6P). The Tps2NTD closely resembles the structure of Tps1 but lacks any catalytic activity. The Tps2PD-BeF3 -trehalose and Tps2PD(D24N)-T6P complex structures reveal a "closed" conformation that is effected by extensive interactions between each trehalose hydroxyl group and residues of the cap and core domains of the protein, thereby providing exquisite substrate specificity. Disruption of any of the direct substrate-protein residue interactions leads to significant or complete loss of phosphatase activity. Notably, the Tps2PD-BeF3 -trehalose complex structure captures an aspartyl-BeF3 covalent adduct, which closely mimics the proposed aspartyl-phosphate intermediate of the phosphatase catalytic cycle. Structures of substrate-free Tps2PD reveal an "open" conformation whereby the cap and core domains separate and visualize the striking conformational changes effected by substrate binding and product release and the role of two hinge regions centered at approximately residues 102-103 and 184-188. Significantly, tps2Δ, tps2NTDAΔ, and tps2D705N strains are unable to grow at elevated temperatures. Combined, these studies provide a deeper understanding of the substrate recognition and catalytic mechanism of Tps2 and provide a structural basis for the future design of novel antifungal compounds against a target found in three major fungal pathogens.

MODIFICATION OF TREHALOSE-6-PHOSPHATE LEVELS IN PLANTS

Compounds which are trehalose-6-phosphate or trehalose-6-phosphonate precursors of formula (I) or agriculturally acceptable salts thereof are provided: (I) The compounds are useful in increasing starch production in plants.

Flow chemistry kinetic studies reveal reaction conditions for ready access to unsymmetrical trehalose analogues

Monofunctionalization of trehalose, a widely-found symmetric plant disaccharide, was studied in a microreactor to give valuable kinetic insights that have allowed improvements in desymmetrization yields and the development of a reaction sequence for large scale monofunctionalizations that allow access to probes of trehalose's biological function.