Methyl beta-D-xyloside

Base Information

• Chemical Name: Methyl beta-D-xyloside
• CAS No.: 612-05-5
• Deprecated CAS: 27072-90-8,27937-21-9
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 29400090
• NSC Number: 403453,400273,170227,126704,232024,78525,25272,1975
• DSSTox Substance ID: DTXSID60939589
• Wikidata: Q82916108
• Mol file: 612-05-5.mol

Synonyms:alpha-methyl-beta-xyloside;beta-methyl-xyloside;methyl xylopyranoside;methyl xylopyranoside, (alpha-D)-isomer;methyl xylopyranoside, (beta-L)-isomer;methyl-D-xylopyranoside

Chemical Property of Methyl beta-D-xyloside

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 155-158 °C
• Refractive Index: 1.51
• Boiling Point: 314 °C at 760 mmHg
• PKA: 13.04±0.70(Predicted)
• Flash Point: 143.7 °C
• PSA: 79.15000
• Density: 1.4 g/cm³
• LogP: -1.92820
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Water Solubility.: almost transparency in Water
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

98%, ^*data from raw suppliers

Methyl b-D-xylopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1C(C(C(CO1)O)O)O
• Uses: Methyl β-D-xylopyranoside has been used in a study to assess tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides. It has also been used in a study that investigated transacetylations to carbohydrates catalyzed by acetylxylan esterase in the presence of an organic solvent.

Technology Process of Methyl beta-D-xyloside

There total 145 articles about Methyl beta-D-xyloside 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: 42.0%

methanol (67-56-1) + D-xylose (58-86-6) → methyl-β-D-xylopyranoside (612-05-5) + methyl-α-D-xylopyranoside (91-09-8)

Guidance literature:

With Dowex-50W X-8H⁺-400; for 10h; Heating;

DOI:10.1021/ol049389b

Reference yield: 15.0%

(1S,3R,4R,6R,7S,10R)-7-Allyloxy-10-hydroxy-3,4-dimethoxy-3,4-dimethyl-2,5,8-trioxabicyclo[4.4.0]decane (201043-05-2) → allyl α-D-xylopyranoside (140420-69-5) + allyl 3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside (201043-07-4) + methyl-β-D-xylopyranoside (612-05-5) + methyl-α-D-xylopyranoside (91-09-8)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; for 168h; Yields of byproduct given; Heating;

Reference yield:

methyl 2,4-di-O-acetyl-β-D-xylopyranoside (74162-08-6) → methyl 2-mono-O-acetyl-β-D-xylopyranoside (41897-35-2,41897-36-3,57800-28-9,61344-52-3,80973-76-8,105260-78-4,138793-60-9,80973-64-4) + methyl-β-D-xylopyranoside (612-05-5)

Guidance literature:

With acetyl esterase TrCE₁₆; water; In aq. phosphate buffer; at 40 ℃; for 4h; pH=6.0; Time; Enzymatic reaction;

DOI:10.1016/j.bbagen.2013.10.008

upstream raw materials:

D-xylose

trimethyl orthoformate

methanol

D-Xylose

Downstream raw materials:

methyl tri-O-benzoyl-α-D-arabinopyranoside

methyl-(O³,O⁴-isopropyliden-α-D-arabinopyranoside)

methyl-(O²,O³-((S)-benzylidene]-β-D-ribofuranoside)

methyl 2,3,4-tri-O-benzoyl-β-D-ribopyranoside

Refernces

• 1、 De Graef, Steff,Gadakh, Bharat,Nautiyal, Manesh,Pang, Luping,Strelkov, Sergei V.,Van Aerschot, Arthur,Vondenhoff, Gaston,Weeks, Stephen D.. "Synthesis and structural insights into the binding mode of the albomycin δ1 core and its analogues in complex with their target aminoacyl-tRNA synthetase". . . Retrieved 2020/07/21.
• 2、 Ushimaru, Richiro,Liu, Hung-Wen. "Biosynthetic Origin of the Atypical Stereochemistry in the Thioheptose Core of Albomycin Nucleoside Antibiotics". supporting information. . Retrieved 2019/02/14.