(1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol

Base Information

• Chemical Name: (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol
• CAS No.: 842133-32-8
• Molecular Formula: C₁₉H₂₃ClO₅S
• Molecular Weight: 398.908
• Mol file: 842133-32-8.mol

Synonyms:(1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol

Chemical Property of (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol

There total 6 articles about (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-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: 87.0%

(4aR,6S,7S,8R,8aR)-2,2-di-tert-butyl-6-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-8-[(t r iisopropylsilyl) oxy]-hexahydropyrano[3,2-d][1,3,2] dioxasilin-7-ol (1547297-56-2) → (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol (842133-32-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 3h;

DOI:10.1248/cpb.c13-00407

Reference yield:

3-bromo-2-(4-ethylbenzyl)thiophene (842135-71-1) → (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol (842133-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 4 h / Reflux

2.1: borane-THF / tetrahydrofuran / 0 °C

2.2: 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; borane-THF; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water;

DOI:10.1248/cpb.c13-00407

Reference yield:

(3-bromo-2-thienyl)(4-ethylphenyl)methanol (842135-70-0) → (1S)-1,5-anhydro-1-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-D-glucitol (842133-32-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 18 h / 0 - 20 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / 1,2-dimethoxyethane; water / 4 h / Reflux

3.1: borane-THF / tetrahydrofuran / 0 °C

3.2: 0 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 60 °C

With aluminum (III) chloride; bis-triphenylphosphine-palladium(II) chloride; lithium aluminium tetrahydride; borane-THF; tetrabutyl ammonium fluoride; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; water;

DOI:10.1248/cpb.c13-00407

upstream raw materials:

(4aR,6S,7S,8R,8aR)-2,2-di-tert-butyl-6-[4-chloro-5-(4-ethylbenzyl)-2-thienyl]-8-[(t r iisopropylsilyl) oxy]-hexahydropyrano[3,2-d][1,3,2] dioxasilin-7-ol

(3-bromo-2-thienyl)(4-ethylphenyl)methanol

3-bromo-2-(4-ethylbenzyl)thiophene

1,5-anhydro-2-deoxy-4,6-O-di-(tert-butyl)silanediyl-3-O-triisopropylsilyl-D-arabino-hex-1-enitolylboronic acid pinacol ester

Refernces