2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose

Base Information

• Chemical Name: 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose
• CAS No.: 333360-88-6
• Molecular Formula: C₄₉H₅₀O₅
• Molecular Weight: 718.933
• Mol file: 333360-88-6.mol

Synonyms:2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose

Chemical Property of 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose

There total 2 articles about 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose 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: 63.0%

2,3,4,6-tetra-O-(pheny lmethy l)-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (1365556-34-8) → 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (333360-88-6)

Guidance literature:

With chlorotriisopropylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -25 ℃; for 2.5h; optical yield given as %de; stereoselective reaction; Large scale reaction;

DOI:10.1021/op200306q

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → 2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (333360-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate / dichloromethane

2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran; hexane / 0.5 h / -75 - -60 °C / Inert atmosphere; Large scale reaction

2.2: -75 - -65 °C / Inert atmosphere

3.1: chlorotriisopropylsilane; boron trifluoride diethyl etherate / acetonitrile / 2.5 h / -25 °C / Large scale reaction

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N,N,N,-tetramethylethylenediamine; chlorotriisopropylsilane; boron trifluoride diethyl etherate; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/op200306q

Reference yield:

2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (333360-88-6) → (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-(phenyl))-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:

2,3,4,6-tetra-O-(phenylmethyl)-1,5-anhydro-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose; With palladium 10% on activated carbon; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

With hydrogen; In tetrahydrofuran; at 20 - 25 ℃; for 4h;

DOI:10.1021/op200306q

upstream raw materials:

2,3,4,6-tetra-O-(pheny lmethy l)-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose

2,3,4,6-Tetra-O-benzyl-D-glucopyranose