Methyl 4-deoxy-α-D-xylo-hexopyranoside

Base Information

• Chemical Name: Methyl 4-deoxy-α-D-xylo-hexopyranoside
• CAS No.: 13241-00-4
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.185
• Mol file: 13241-00-4.mol

Synonyms:Methyl 4-Deoxy-a-D-glucopyranoside;Methyl 4-Deoxy-;Methyl 4-Deoxy-α-D-glucopyranoside

Chemical Property of Methyl 4-deoxy-α-D-xylo-hexopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 90 °C
• Boiling Point: 349.268°C at 760 mmHg
• PKA: 13.22±0.70(Predicted)
• Flash Point: 165.032°C
• PSA: 79.15000
• Density: 1.332g/cm³
• LogP: -1.53810
• Solubility.: Methanol, Water

Purity/Quality:

95% ^*data from raw suppliers

Methyl 4-deoxy-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: This compound has been shown to stimulate gustatory receptors, specifically those responsible for sweet taste in mammalian biochemical studies. It is also an intermediate for the synthesis of 4-Deoxy-D-glucose.

Technology Process of Methyl 4-deoxy-α-D-xylo-hexopyranoside

There total 19 articles about Methyl 4-deoxy-α-D-xylo-hexopyranoside 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: 88.0%

Methyl-2,3,6-tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranosid (19488-41-6) → methyl 4-deoxy-α-D-xylo-hexopyranoside (13241-00-4)

Guidance literature:

With sodium methylate; In methanol; for 48h; Ambient temperature;

DOI:10.1139/v90-288

Reference yield:

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3) → methyl 4-deoxy-α-D-xylo-hexopyranoside (13241-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂

2: tributylstannane; AIBN / toluene

3: Na; methanol

With pyridine; methanol; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium; In dichloromethane; toluene;

DOI:10.1016/j.tetasy.2004.12.004

Reference yield:

(+/-)-methyl 5-O-benzyl-4-deoxy-lyxo-DL-hexonate (128503-22-0,147048-87-1) → (+/-)-methyl 4-deoxy-DL-lyxo-hexopyranoside (13241-00-4,33962-47-9,33982-05-7,33982-06-8,42821-89-6,51385-57-0,67308-46-7,124252-87-5,125287-87-8,147127-93-3,147127-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1: SnCl₂ / dioxane / 24 h / 20 °C

2: imidazole / dimethylformamide / 0 °C

3: DIBAL / toluene / -65 °C

4: 1) H₂, 2) acidic DOWEX / 1) 10percent Pd/C / 1) methanol, 1 atm., 20 deg C, 2) methanol, reflux, 3 h

With 1H-imidazole; acidic DOWEX; hydrogen; diisobutylaluminium hydride; tin(ll) chloride; palladium on activated charcoal; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)88356-3

upstream raw materials:

Methyl-2,3,6-tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranosid

methyl 3,4-O-thiocarbonyl-α-D-galactopyranoside di-O-acetate

methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside

Methyl-2,3,6-tri-O-benzoyl-4-O-phenoxythiocarbonyl-α-D-galactopyranosid

Downstream raw materials:

Methyl 2,3,6-tri-O-acetyl-4-deoxy-α-D-glucopyranoside

phenyl 2,3,6-tri-O-acetyl-4-deoxy-1-thio-β-D-xylo-hexoside

2,4-dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-β-D-xylo-hexopyranoside

4-deoxy-D-xylo-hexose

Refernces

• 1、 Stick, Robert V.,Stubbs, Keith A.. "From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides". . p. 321 - 335. Retrieved 2007/10/03.
• 2、 Berven,Dolphin,Withers. "The base-catalysed anomerization of dinitrophenyl glycosides: Evidence for a novel reaction mechanism". . p. 1859 - 1866. Retrieved 2007/10/02.