Glucose-1-methylenephosphonate

Base Information

• Chemical Name: Glucose-1-methylenephosphonate
• CAS No.: 82977-27-3
• Molecular Formula: C₇H₁₅O₈P
• Molecular Weight: 258.165
• Mol file: 82977-27-3.mol

Synonyms:((2R,3R,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid;

Chemical Property of Glucose-1-methylenephosphonate

Chemical Property:

• Boiling Point: 606.8±65.0 °C(Predicted)
• PKA: 2.24±0.10(Predicted)
• PSA: 157.49000
• Density: 1.753±0.06 g/cm3(Predicted)
• LogP: -2.99350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Glucose-1-methylenephosphonate

There total 3 articles about Glucose-1-methylenephosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1-deoxy-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)methanephosphonic acid (82933-04-8) → (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid (82977-27-3)

Guidance literature:

With Dowex 2 (OH^(1-)form) resin; In methanol; Ambient temperature;

DOI:10.1021/jo00144a011

Reference yield:

2,6-anhydro-1-bromo-1-deoxy-3,4,5,7-tetra-O-acetyl-D-glycero-D-gluco-heptitol (34010-30-5) → (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid (82977-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 6 h / Heating

2: 67 percent / Me₃SiI / CCl₄ / 0.5 h / 0 °C

3: Dowex 2 (OH^(1-)form) resin / methanol / Ambient temperature

With trimethylsilyl iodide; Dowex 2 (OH^(1-)form) resin; In methanol; tetrachloromethane;

DOI:10.1021/jo00144a011

Reference yield:

diethyl (1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methanephosphonate (82933-03-7) → (1-deoxy-β-D-glucopyranosyl)methanephosphonic acid (82977-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / Me₃SiI / CCl₄ / 0.5 h / 0 °C

2: Dowex 2 (OH^(1-)form) resin / methanol / Ambient temperature

With trimethylsilyl iodide; Dowex 2 (OH^(1-)form) resin; In methanol; tetrachloromethane;

DOI:10.1021/jo00144a011

upstream raw materials:

(1-deoxy-2,3,4-tri-O-acetyl-β-D-glucopyranosyl)methanephosphonic acid

2,6-anhydro-1-bromo-1-deoxy-3,4,5,7-tetra-O-acetyl-D-glycero-D-gluco-heptitol

diethyl (1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methanephosphonate

Refernces