D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-

Base Information

• Chemical Name: D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-
• CAS No.: 1034305-21-9
• Molecular Formula: C29H29FO9S
• Molecular Weight: 572.608
• Mol file: 1034305-21-9.mol

Synonyms:D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-;(1S)-1,5-Anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-D-glucitol 2,3,4,6-tetraacetate;(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-D-glucitol

Chemical Property of D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-

Chemical Property:

• Boiling Point: 634.8±55.0 °C(Predicted)
• PSA: 142.67000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 4.42930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)-

There total 5 articles about D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylMethyl)-4-fluorophenyl]-, 2,3,4,6-tetraacetate, (1S)- 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:

methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside (1034305-27-5) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol (1034305-21-9)

Guidance literature:

With trifluorormethanesulfonic acid; tert-butyldimethylsilane; In toluene; acetonitrile; at -9.2 - 1 ℃;

Reference yield:

C21H21FO6S + acetic anhydride (108-24-7) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol (1034305-21-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 25 ℃; for 2h; Temperature; Industrial scale;

Reference yield:

2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene (1034305-17-3) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol (1034305-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: s-butylmagnesium chloride; n-butyllithium; lithium chloride / tetrahydrofuran; hexane / 3.17 h / -10 °C / Inert atmosphere; Industrial scale

1.2: 3 h / -10 °C / Industrial scale

2.1: pyridine; dmap / dichloromethane / 2 h / 25 °C / Industrial scale

With pyridine; dmap; n-butyllithium; s-butylmagnesium chloride; lithium chloride; In tetrahydrofuran; hexane; dichloromethane;

upstream raw materials:

methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside

acetic anhydride

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

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

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