Methyl 2,3,5-tri-O-benzylpentofuranoside

Base Information

• Chemical Name: Methyl 2,3,5-tri-O-benzylpentofuranoside
• CAS No.: 79083-43-5
• Molecular Formula: C27H30 O5
• Molecular Weight: 434.5241
• NSC Number: 80726
• DSSTox Substance ID: DTXSID201000253
• Mol file: 79083-43-5.mol

Synonyms:NSC80726;Methyl 2,3,5-tri-O-benzylpentofuranoside;DTXSID201000253;BCP31778;NSC-80726;FT-0672259;FT-0698750;D-Ribofuranoside, Methyl 2,3,5-tris-O-(phenylMethyl)-;(2R,3R,4R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran

Chemical Property of Methyl 2,3,5-tri-O-benzylpentofuranoside

Chemical Property:

• Vapor Pressure: 1.09E-11mmHg at 25°C
• Boiling Point: 552.6°C at 760 mmHg
• Flash Point: 217.4°C
• PSA: 63.22000
• Density: 1.17g/cm³
• LogP: 4.38550
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 434.20932405
• Heavy Atom Count: 32
• Complexity: 496

Purity/Quality:

99% ^*data from raw suppliers

METHYL TRI-O-BENZYL-ALPHA-D-ARABINOFURANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of Methyl 2,3,5-tri-O-benzylpentofuranoside

There total 22 articles about Methyl 2,3,5-tri-O-benzylpentofuranoside 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: 100.0%

benzyl bromide (100-39-0) + methyl 3,5-di-O-benzyl-α-D-ribofuranoside (191543-71-2) → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5,79083-29-7,79083-32-2,79083-33-3,79083-40-2,79083-41-3,79083-43-5,79083-44-6,85549-73-1,85610-74-8,89824-86-2,131615-65-1,131896-99-6,135910-14-4,135911-60-3,55725-85-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1246/bcsj.74.1679

Reference yield: 98.0%

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) + Trimethylmethoxysilane (1825-61-2) → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5,79083-29-7,79083-32-2,79083-33-3,79083-40-2,79083-41-3,79083-43-5,79083-44-6,85549-73-1,85610-74-8,89824-86-2,131615-65-1,131896-99-6,135910-14-4,135911-60-3,55725-85-4)

Guidance literature:

With trifluoromethylsulfonic anhydride; diphenyltin sulfide; cesium fluoride; In diethyl ether;

Reference yield: 89.0%

benzyl chloride (100-44-7) + methyl D-arabinofuranoside (56607-40-0) → methyl 2,3,5-tri-O-benzyl-α-D-arabinofuranoside (79083-43-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 10h; Heating;

upstream raw materials:

benzyl chloride

methyl D-arabinofuranoside

methyl D-arabinofuranoside

methanol

Downstream raw materials:

(2R,3R,4R)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol

(1S,2S,3R,4R)-2,3,5-tris(benzyloxy)-1-methoxy-1-(phenylthio)pentan-4-ol

(2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran

(2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol

Refernces

• 1、 Suthagar, Kajitha,Polson, Matthew I. J.,Fairbanks, Antony J.. "Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates". . p. 6573 - 6579. Retrieved 2015/06/16.
• 2、 Lou, Chenguang,Xiao, Qiang,Brennan, Lavinia,Light, Mark E,Vergara-Irigaray, Nuria,Atkinson, Elizabeth M.,Holden-Dye, Lindy M.,Fox, Keith R.,Brown, Tom. "Synthesis and properties of triplex-forming oligonucleotides containing 2′-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine". experimental part. p. 6389 - 6397. Retrieved 2010/10/05.