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

Base Information

• Chemical Name: 2,3,4,6-tetra-O-(pheny lmethy l)-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose
• CAS No.: 1365556-34-8
• Molecular Formula: C₄₉H₅₀O₆
• Molecular Weight: 734.932
• Mol file: 1365556-34-8.mol

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

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

There total 2 articles about 2,3,4,6-tetra-O-(pheny lmethy l)-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: 59.4%

3-bromo-(4'-ethyl)-diphenylmethane (333360-86-4) + (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2,3,4,6-tetra-O-(pheny lmethy l)-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (1365556-34-8)

Guidance literature:

3-bromo-(4'-ethyl)-diphenylmethane; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -75 - -60 ℃; for 0.5h; Inert atmosphere; Large scale reaction;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; at -75 - -65 ℃; Inert atmosphere;

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-(pheny lmethy l)-1-C-[3-[(4-ethylphenyl)methyl]phenyl]glucopyranose (1365556-34-8)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/op200306q

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

upstream raw materials:

3-bromo-(4'-ethyl)-diphenylmethane

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

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

Downstream raw materials:

(2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-(phenyl))-6-hydroxymethyl-tetrahydro-2H-pyran-3,4,5-triol L-phenylalanine

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