(S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide

Base Information

• Chemical Name: (S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide
• CAS No.: 27304-75-2
• Molecular Formula: C16H20 N2 O2 S
• Molecular Weight: 304.413
• DSSTox Substance ID: DTXSID50350784
• Wikidata: Q82126886
• Mol file: 27304-75-2.mol

Synonyms:(S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide;27304-75-2;(1S)-1-phenyl-N-[[(1S)-1-phenylethyl]sulfamoyl]ethanamine;N,N'-Bis[(1S)-1-phenylethyl]-Sulfamide;DTXSID50350784;(S,S)-(-)-N,N-Bis(a-methyl-benzyl)*sulf amide;(S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide, 99%;(S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide, purum, >=98.0% (sum of enantiomers, TLC)

Chemical Property of (S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide

Chemical Property:

• Melting Point: 98-100 °C(lit.)
• Boiling Point: 450.2°Cat760mmHg
• Flash Point: 226.1°C
• PSA: 66.58000
• Density: 1.188g/cm³
• LogP: 4.79540
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 304.12454906
• Heavy Atom Count: 21
• Complexity: 361

Purity/Quality:

97% ^*data from raw suppliers

(S,S)-(-)-N,N'-BIS(ALPHA-METHYLBENZYL)SULFAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NS(=O)(=O)NC(C)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)NS(=O)(=O)N[C@@H](C)C2=CC=CC=C2
• General Description: (S,S)-(-)-N,N'-BIS(ALPHA-METHYLBENZYL)SULFAMIDE, also known as Sharpless' reagent, is a chiral ligand used in asymmetric reductions. It facilitates the enantioselective reduction of prochiral ketones when combined with lithium aluminum hydride (LiAlH4) and N-benzylmethylamine, achieving high stereoselectivity at low temperatures (-20°C). (S,S)-(-)-N,N'-BIS(ALPHA-METHYLBENZYL)SULFAMIDE is valued for its accessibility and effectiveness in producing chiral alcohols with controlled stereochemistry.

Technology Process of (S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide

There total 1 articles about (S,S)-(-)-N,N'-Bis(alpha-methylbenzyl)sulfamide 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: 89.0%

(S)-1-phenyl-ethylamine (2627-86-3) → (S,S)-threo-N,N'-bis(α-methylbenzyl)sulfamide (27304-75-2)

Guidance literature:

With sulfuryl dichloride; triethylamine; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/jo00194a048

upstream raw materials:

(S)-1-phenyl-ethylamine