Methyl beta-D-ribofuranoside

Base Information

• Chemical Name: Methyl beta-D-ribofuranoside
• CAS No.: 7473-45-2
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 29329990
• European Community (EC) Number: 231-271-5
• DSSTox Substance ID: DTXSID301312174
• Nikkaji Number: J278.878K
• Wikidata: Q63409835
• Mol file: 7473-45-2.mol

Synonyms:Methyl beta-D-ribofuranoside;7473-45-2;Methyl b-D-Ribofuranoside;(2R,3S,4R,5R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol;(2R,3S,4R,5R)-2-(Hydroxymethyl)-5-methoxy-tetrahydrofuran-3,4-diol;EINECS 231-271-5;MFCD00047075;Methyl pentofuranoside #;Methyl .beta.-D-ribofuranoside;Ribofuranoside, methyl, .beta.-D-;NSC 400285;methyl -d-ribofuranoside;Methyl ?-D-Ribofuranoside;SCHEMBL271445;DTXSID301312174;(2R,3S,4R,5R)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol;Methyl beta-D-ribofuranoside, 97%;BBL102872;STL556680;AKOS006344687;MS-20513;A838212;Q63409835

Chemical Property of Methyl beta-D-ribofuranoside

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 3.01E-06mmHg at 25°C
• Melting Point: 78 °C
• Refractive Index: -51 ° (C=2, H2O)
• Boiling Point: 348.7 °C at 760 mmHg
• PKA: 13.14±0.70(Predicted)
• Flash Point: 164.7 °C
• PSA: 79.15000
• Density: 1.4 g/cm³
• LogP: -1.92820
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water (Slightly, Sonicated)
• Water Solubility.: Soluble in water
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(O1)CO)O)O
• Isomeric SMILES: CO[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Uses: D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography.

Technology Process of Methyl beta-D-ribofuranoside

There total 57 articles about Methyl beta-D-ribofuranoside 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: 93.0%

2,3,5-tri-O-acetyl-1-O-methyl-β-D-ribofuranose (37077-80-8,110415-62-8) → 1-O-methyl-D-ribofuranose (7473-45-2)

Guidance literature:

With tris(2,4,6-trimethoxyphenyl)phosphine; In methanol; at 20 ℃; for 28h;

DOI:10.1246/cl.2001.934

Reference yield: 90.0%

methanol (67-56-1) + 1-azido-2,3,4-tri-O-acetylribose (70964-85-1) → 1-O-methyl-D-ribofuranose (7473-45-2)

Guidance literature:

With sodium; for 12h; Ambient temperature;

Reference yield: 89.0%

methanol (67-56-1) + (2R,3R,4S,5R)-2-azido-5-hydroxymethyl-tetrahydro-furan-3,4-diol (51970-31-1) → 1-O-methyl-D-ribofuranose (7473-45-2)

Guidance literature:

With sodium; 1.) reflux, 3 h, 2.) RT, overnight;

upstream raw materials:

methanol

D-ribose

(2R,3R,4S,5R)-2-azido-5-hydroxymethyl-tetrahydro-furan-3,4-diol

D-Ribose

Downstream raw materials:

methyl 2,3,5-tri-O-benzyl-D-ribofuranoside

2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside

2,3,5-tri-O-benzyl-1-O-methyl-α-D-xylofuranoside

2,3,5-tri-O-benzyl-1-O-methyl-β-D-xylofuranoside

Refernces

• 1、 écija, Patricia,Uriarte, Iciar,Spada, Lorenzo,Davis, Benjamin G.,Caminati, Walther,Basterretxea, Francisco J.,Lesarri, Alberto,Cocinero, Emilio J.. "Furanosic forms of sugars: Conformational equilibrium of methyl β-d-ribofuranoside". . p. 6241 - 6244. Retrieved 2016.
• 2、 -. "MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF". Page/Page column 119-121. . Retrieved 2021/02/19.
• 3、 Oka, Natsuhisa,Mori, Ayumi,Suzuki, Kanna,Ando, Kaori. "Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones". . p. 657 - 673. Retrieved 2020/12/23.