2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride

Base Information

• Chemical Name: 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride
• CAS No.: 86883-42-3
• Molecular Formula: C₂₆H₂₇FO₄
• Molecular Weight: 422.496
• Mol file: 86883-42-3.mol

Synonyms:2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride

Chemical Property of 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride

There total 5 articles about 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride 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: 95.0%

2,3,5-tri-O-benzyl-L-arabinofuranose (96192-07-3) → (2S,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-fluoro-tetrahydro-furan (86883-41-2,86883-42-3,86883-51-4,94898-40-5,94898-52-9,96089-61-1,114762-38-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; for 0.333333h; Ambient temperature; addition at -30 deg C;

DOI:10.1016/S0040-4039(00)98451-X

Reference yield: 72.0%

2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride (86883-41-2) → 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride (86883-42-3)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; for 0.166667h; Ambient temperature;

DOI:10.1246/cl.1983.935

Reference yield: 64.0%

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) → 2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride (86883-42-3)

Guidance literature:

With diethylamino-sulfur trifluoride; In tetrahydrofuran; at -30 - 20 ℃; for 0.333333h;

DOI:10.1016/j.carres.2018.04.008

upstream raw materials:

2,3,5-tri-O-benzyl-α-D-ribofuranosyl fluoride

(3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)tetrahydrofuran-2-yl acetate

2,3,5-tri-O-benzyl-D-ribofuranose

2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranose

Downstream raw materials:

methyl 6-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-α-D-glucopyranoside

Refernces

• 1、 Bannykh, Anton,Khomutnyk, Yaroslav,Kim, Sungjin,Nagorny, Pavel. "Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride". supporting information. p. 190 - 194. Retrieved 2021/01/13.
• 2、 Hayashi, Masahiko,Hashimoto, Shun-ichi,Noyori, Ryoji. "SIMPLE SYNTHESIS OF GLYCOSYL FLUORIDES". . p. 1747 - 1750. Retrieved 2007/10/02.