(1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate

Base Information

• Chemical Name: (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate
• CAS No.: 197244-91-0
• Molecular Formula: C14H11 N O7 S
• Molecular Weight: 337.3
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90391651
• Nikkaji Number: J899.957K
• Wikidata: Q82189267
• Mol file: 197244-91-0.mol

Synonyms:197244-91-0;(1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate;Bsmoc-OSu;(1,1-dioxo-1-benzothiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate;1,1-Dioxobenzo[b]thiophen-2-ylmethyl N-succinimidyl carbonate;Carbonic acid, (1,1-dioxidobenzo[b]thien-2-yl)methyl 2,5-dioxo-1-pyrrolidinyl ester;DTXSID90391651;AKOS015910698;AS-76848;FT-0696251;I11989;J-012748;N-(Benzo[b]thiophenesulfone-2-methoxycarbonyl)succinimide;1,1-DIOXOBENZO[B]THIOPHEN-2-YLMETHYL N-SUCCIMIDYL CARBONATE;(1,1-Dioxidobenzo[b]thiophen-2-yl)methyl(2,5-dioxopyrrolidin-1-yl)carbonate;(1,1-Dioxidobenzo[b]thiophen-2-yl)methyl-(2,5-dioxopyrrolidin-1-yl) carbonate;2-[[(2,5-Dioxopyrrolizinooxy)carbonyloxy]methyl]benzo[b]thiophene 1,1-dioxide;Carbonic acid,(1,1-dioxidobenzo[b]thien-2-yl)methyl 2,5-dioxo-1-pyrrolidinyl ester

Chemical Property of (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate

Chemical Property:

• Vapor Pressure: 6.6E-12mmHg at 25°C
• Melting Point: ~165 °C (dec.)
• Boiling Point: 544.3oC at 760 mmHg
• Flash Point: 283oC
• PSA: 115.43000
• Density: 1.63g/cm3
• LogP: 2.05070
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 337.02562286
• Heavy Atom Count: 23
• Complexity: 660

Purity/Quality:

99%, ^*data from raw suppliers

(1,1-Dioxidobenzo[b]thiophen-2-yl)methyl-(2,5-dioxopyrrolidin-1-yl) carbonate 95+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2=CC3=CC=CC=C3S2(=O)=O
• Uses: (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl-(2,5-dioxopyrrolidin-1-yl) Carbonate is a therapeutic monosaccharide-based inhibitors of hexokinase and glucokinase for parasitic diseases, along with methods of their formation and use.

Technology Process of (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate

There total 5 articles about (1,1-Dioxidobenzo[b]thiophen-2-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate 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: 74.0%

dicyclohexylamine salt of N-hydroxysuccinimide (82911-72-6) + 1,1-dioxobenzo[b]thiophen-2-ylmethyl chloroformate (135204-19-2) → N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate (197244-91-0)

Guidance literature:

In dichloromethane; for 20h;

DOI:10.1021/jo982140l

Reference yield:

benzothiophen-2-yllithium (50779-55-0) → N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate (197244-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) NaBH₄ / 2.) MeOH

2: 75 percent / sodium perborate tetrahydrate / acetic acid / 45 - 50 °C

3: 36.1 g / tetrahydrofuran / -30 - 20 °C

4: 74 percent / CH₂Cl₂ / 20 h

With sodium perborate; sodium tetrahydroborate; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/jo982140l

Reference yield:

benzothiophene-2-methanol (17890-56-1) → N-(benzothiophenesulfone-2-methyl)-N-succinimidyl carbonate (197244-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / sodium perborate tetrahydrate / acetic acid / 45 - 50 °C

2: 36.1 g / tetrahydrofuran / -30 - 20 °C

3: 74 percent / CH₂Cl₂ / 20 h

With sodium perborate; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/jo982140l

upstream raw materials:

dicyclohexylamine salt of N-hydroxysuccinimide

1,1-dioxobenzo[b]thiophen-2-ylmethyl chloroformate

benzothiophen-2-yllithium

benzothiophene-2-methanol

Downstream raw materials:

Bsmoc-Met-OH

Bsmoc-Asn-OH

Bsmoc-Tyr(t-Bu)-OH

Bsmoc-Asn(Trt)-OH