2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose
• CAS No.: 138385-37-2
• Molecular Formula: C₃₇H₃₉NO₅
• Molecular Weight: 577.72
• Mol file: 138385-37-2.mol

Synonyms:2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose

Chemical Property of 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose

There total 6 articles about 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose 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: 87.0%

(2S,3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-2-[3-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-tetrahydro-furan-2-ol → 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose (138385-37-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 10 ℃;

DOI:10.1021/jm00081a012

Reference yield: 50.0%

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline (51849-84-4) + (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one (14233-64-8,134307-32-7,55094-52-5) → 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose (138385-37-2)

Guidance literature:

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline; (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one; With n-butyllithium; In tetrahydrofuran; at -75 ℃; Inert atmosphere;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jacs.1c01302

Reference yield:

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline (51849-84-4) → 2,3,5-tri-O-benzyl-1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose (138385-37-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -85 deg C, 20 deg C, 2.) THF, hexane, from -85 to -30 deg C, 3 h

2: 87 percent / BF₃*OEt₂, triethylsilane / CH₂Cl₂ / -78 - 10 °C

With triethylsilane; n-butyllithium; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1021/jm00081a012

upstream raw materials:

2-(3-bromophenyl)-4,4-dimethyl-2-oxazoline

(3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one

m-bromobenzoic aldehyde

2-{[1-(3-Bromo-phenyl)-meth-(Z)-ylidene]-amino}-2-methyl-propan-1-ol

Downstream raw materials:

3-(2,3,5-tri-O-benzyl-1-deoxy-β-D-ribofuranosyl)benzoic acid

3-(1-deoxy-β-D-ribofuranosyl)benzoic acid

1-deoxy-1-<3-(4,5-dihydro-4,4-dimethyl-2-oxazol-2-yl)phenyl>-β-D-ribofuranose

methyl 3-(2,3,5-tri-O-benzyl-1-deoxy-β-D-ribofuranosyl)benzoate