(R)-(-)-Glycidyl-4-nitrobenzenesulfonate

Base Information

• Chemical Name: (R)-(-)-Glycidyl-4-nitrobenzenesulfonate
• CAS No.: 123750-60-7
• Molecular Formula: C9H9 N O6 S
• Molecular Weight: 259.24
• Hs Code.: 2910900090
• European Community (EC) Number: 681-216-8
• Nikkaji Number: J1.559.656B
• Mol file: 123750-60-7.mol

Synonyms:123750-60-7;(R)-(-)-Glycidyl-4-nitrobenzenesulfonate;(R)-Oxiran-2-ylmethyl 4-nitrobenzenesulfonate;Benzenesulfonic acid, 4-nitro-, (2R)-2-oxiranylmethyl ester;Glycidyl (R)-(-)-4-nitrobenzenesulfonate;118629-64-4;[(2R)-oxiran-2-yl]methyl 4-nitrobenzenesulfonate;(R)-Glycidyl-4-nitrobenzenesulfonate;[(2R)-oxiran-2-yl]methyl 4-nitrobenzene-1-sulfonate;(R)-Glycidyl 4-nitrobenzene sulfonate;(r)-glycidylnosylate;SCHEMBL9645456;Benzenesulfonic acid, 4-nitro-, (2R)-oxiranylmethyl ester;Benzenesulfonic acid,4-nitro-,(2R)-2-oxiranylmethyl ester;CXYDYDCHYJXOEY-MRVPVSSYSA-N;MFCD08460169;AKOS025401460;AC-18294;AS-70773;(R)-Oxiran-2-ylmethyl4-nitrobenzenesulfonate;A890652

Chemical Property of (R)-(-)-Glycidyl-4-nitrobenzenesulfonate

Chemical Property:

• PSA: 110.10000
• LogP: 2.30290
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 259.01505818
• Heavy Atom Count: 17
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

R-GlycidylNosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)COS(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: C1[C@@H](O1)COS(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Uses: R-Glycidyl Nosylate is used as the chiral pool reactant to prepare C3-symmetric precursor 9.

Technology Process of (R)-(-)-Glycidyl-4-nitrobenzenesulfonate

There total 3 articles about (R)-(-)-Glycidyl-4-nitrobenzenesulfonate 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: 58.0%

4-Nitrobenzenesulfonyl chloride (98-74-8) + (S)-oxiranemethanol (60456-23-7) → (2R)-glycidyl 4-nitrobenzenesulfonate (123750-60-7,118629-64-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jm900563e

Reference yield:

4-Nitrobenzenesulfonyl chloride (98-74-8) + (S)-oxiranemethanol (60456-23-7) → S-oxiran-2-ylmethyl 4-nitrobenzenesulfonate (118712-60-0,118629-64-4) + (2R)-glycidyl 4-nitrobenzenesulfonate (123750-60-7,118629-64-4)

Guidance literature:

With triethylamine; In toluene; at -10 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00267a014

Reference yield:

→ (2R)-glycidyl 4-nitrobenzenesulfonate (123750-60-7,118629-64-4)

Guidance literature:

upstream raw materials:

4-Nitrobenzenesulfonyl chloride

(S)-oxiranemethanol

Downstream raw materials:

(2S)-2-isopropoxy-3-[3-[(2S)-2-oxirane-2-ylmethoxy]phenyl]propionic acid ethyl

(R)-(-)-3-(2-cyanophenoxy)-1,2-epoxypropane

(R)-2-((3-bromophenoxy)methyl)oxirane

(+)-(1S)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole

Refernces

• 1、 Klunder, Janice M.,Onami, Tetsuo,Sharpless, K. Barry. "Arenesulfonate Derivatives of Homochiral Glycidol: Versatile Chiral Building Blocks for Organic Synthesis". . p. 1295 - 1304. Retrieved 2007/10/02.