(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

Base Information

• Chemical Name: (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol
• CAS No.: 761423-01-2
• Molecular Formula: C₄₉H₄₅FO₅S
• Molecular Weight: 764.958
• Mol file: 761423-01-2.mol

Synonyms:(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

Chemical Property of (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

Chemical Property:

Purity/Quality:

95%-98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol

There total 10 articles about (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol 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: 86.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4) + 2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene (1034305-17-3) → (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol (761423-01-2)

Guidance literature:

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene; With n-butyllithium; In n-heptane; dibutyl ether; toluene; at -40 ℃; for 2h; Inert atmosphere;

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide; In dibutyl ether; at 20 - 90 ℃; for 2h; Temperature;

Reference yield: 61.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + 2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene (1034305-17-3) → (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol (761423-01-2)

Guidance literature:

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene; With n-butyllithium; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 0.166667h;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; toluene; at -78 ℃; for 2h; Further stages;

DOI:10.1016/j.bmc.2012.03.051

Reference yield: 30.2%

1-C-{3-[1-benzothien-2-yl(hydroxy)methyl]-4-fluorophenyl}-2,3,4,6-tetra-O-benzyl-D-glucopyranose → (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol (761423-01-2)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃; for 5h; Inert atmosphere;

upstream raw materials:

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

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene

(1-benzothiophen-2-yl)(5-bromo-2-fluorophenyl)methanol

5-bromo-2-fluorobenzaldehyde

Downstream raw materials:

(2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol