139059-69-1

Basic information

• Product Name: 7-Oxa-4-thia-3,5-diazanonanoic acid, 8,8-dimethyl-4,4-dioxido-6-oxo-2-(phenylmethyl)-, methyl ester, (S)-
• CAS NO: 139059-69-1
• Molecular Formula: C15H22N2O6S
• Molecular Weight: 358.415
• Mol File: 139059-69-1.mol

Chemical Properties

• CAS DataBase Reference: 7-Oxa-4-thia-3,5-diazanonanoic acid, 8,8-dimethyl-4,4-dioxido-6-oxo-2-(phenylmethyl)-, methyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Oxa-4-thia-3,5-diazanonanoic acid, 8,8-dimethyl-4,4-dioxido-6-oxo-2-(phenylmethyl)-, methyl ester, (S)-(139059-69-1)
• EPA Substance Registry System: 7-Oxa-4-thia-3,5-diazanonanoic acid, 8,8-dimethyl-4,4-dioxido-6-oxo-2-(phenylmethyl)-, methyl ester, (S)-(139059-69-1)

Safety Data

• Hazardous Substances Data: 139059-69-1(Hazardous Substances Data)

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 147000-89-3 N-tert-butyloxycarbonylsulfamoyl chloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 172945-95-8 C₂₅H₃₄N₄O₁₀S 
• 147715-89-7 <(S)(+)> methyl -phenylalaninate 
• 1026261-62-0 C₂₀H₃₀N₂O₈S 
• 1027948-81-7 C₂₄H₃₀N₂O₈S 
• 249539-20-6 (4S)-5-acetyl-4-benzyl-2-(benzyloxycarbonyl)-1-methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide 
• 249538-96-3 N-[(2R)-2-(benzyloxycarbonyl)ethyl]-N'-[(2'S)-2'-(methoxycarbonyl)phenethyl]sulfamide 
• 249538-93-0 N-(benzyloxycarbonylmethyl)-N'-[(2'S)-2'-(methoxycarbonyl)phenethyl]sulfamide 
• 249539-07-9 (4S)-2-[4-benzyl-2-(benzyloxycarbonyl)ethyl]-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide 
• 249539-09-1 (4S)-4-benzyl-2-(benzyloxycarbonyl)methyl-3-oxo-1,2,5-thiadiazolidine 1,1-dioxide 
• 249538-94-1 N-[(2R)-2-(ethoxycarbonyl)ethyl]-N'-[(2'S)-2'-(methoxycarbonyl)phenethyl]sulfamide 
• 323178-29-6 2-(2S)-[(2,3,6,7-tetrahydro-1,2,7-thiadiazepine-1,1-dioxido-7-tert-butyloxycarbonyl-2-yl)]-3-phenylpropionic acid methyl ester 
• 323178-30-9 (S)-2-(1,1-dioxo-1,3,6,7-tetrahydro-1λ⁶-[1,2,7]thiadiazepin-2-yl)-3-phenylpropionic acid methyl ester 
• 323178-28-5 N,N'-bis(2-propenyl)-N-(tert-butoxycarbonylsulfonyl)-L-phenylalanine methyl ester 
• 1026343-26-9 C₂₅H₃₂N₂O₈S 

Relevant articles and documents

Preparation of Sulfamates and Sulfamides Using a Selective Sulfamoylation Agent

Sulfamates and sulfamides are prevalent in biological molecules, but their universal synthetic methods are limited. We herein report a sulfamoylation agent with high solubility and shelf stability. Various sulfamates and sulfamides can be synthesized directly from alcohols or amines by employing this agent with high selectivity and high yields. This protocol was also successfully used for late-stage sulfamoylation of pharmaceuticals containing a hydroxyl or amino group.

Synthesis of 1,2,5-thiadiazolidines 1,1-dioxides (Cyclosulfamides) starting from amino acids and chlorosulfonyl isocyanate

We report here a practical access to a series of five-membered cyclosulfamides (1,2,5-thiadiazolidines 1,1-dioxides) N2 substituted by the BOC group. These compounds are synthesized starting from chlorosulfonyl isocyanate and nitrogen mustards or amino acids. The derivatization of amino acids can lead to an alkyl group on C-4 with a well-defined configuration; in this case the N5 position was protected by a benzyl group. These compounds are valuable tools for asymmetric synthesis. (C) 2000 Elsevier Science Ltd.

Sulfahydantoins as tripeptide constraints: Synthesis and structure of chiral substituted 3-oxo-1,2,5-thiadiazolidine 1,1-dioxides

A sulfahydantoin (3-oxo-1,2,5-thiadiazohdine 1,1-dioxides) motif is used as a new type of peptidic constraint to lock two consecutive amide nitrogens by a sulfonyl bridge. The 5membered heterocyclic motif was prepared starting from proteogenic and synthetic amino acids and chlorosulfonyl isocyanate. Constrained dipeptides were obtained under alkaline conditions (methoxide or tert-butoxide) by cyclization of symmetric and dissymmetric sulfamides. The absolute configuration of the chiral centers for the derivative L-Phe-D-Ala, a congener of the series, was established by X-ray diffraction crystallographic analysis. In addition, the chemo-, regio-, and stereoselectivities of the reactions were studied. In the acylated derivatives, the sulfahydantoin constraint induces a unique backbone conformation with coplanarity of two consecutive peptide bonds.

Synthesis of pseudonucleosides containing chiral sulfahydantoins as aglycone (II)

A series of chiral sulfahydantoins have been synthesized by alkaline cyclization starting from N-sulfamylaminoacid methyl esters. Regioselective glycosylation of these pseudopyrimidic heterocycles was carried out with a benzyl protecting group on the N-su

Nucleopeptidic bioconjugates containing a sulfamide bridge: Linkage via the Mitsunobu reaction

The synthesis of compounds connecting unprotected 2'-deoxyribonucleosides (T,dC,dG,dA) with N-Boc sulfamoyl derivatives of natural aminoacid esters (Phe, Asp) was carried out by Mitsunobu reaction, using regiospecific coupling. The created link was a prio

SYNTHESE ET CYCLISATION DE CARBOXYLSULFAMIDES DERIVES D'AMINOACIDES

3-Oxo-4-substituted-1,2,5-thiazolidine 1,1-dioxides are synthesized from the carbosulfamides of amino acids.