125664-95-1

Basic information

• Product Name: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM
• Synonyms: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM;1-((3aS,6R,7aR)-8,8-DiMethyl-2,2-dioxidohexahydro-1H-3a,6-Methanobenzo[c]isothiazol-1-yl)propan-1-one;(R)-(-)-Propionyl-2,10-camphorsultam
• CAS NO: 125664-95-1
• Molecular Formula: C₁₃H₂₁NO₃S
• Molecular Weight: 271.38
• Product Categories: Peptide
• Mol File: 125664-95-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 153-154 °C(Solv: methanol (67-56-1))
• Boiling Point: 384.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: -14.14±0.40(Predicted)
• CAS DataBase Reference: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(CAS DataBase Reference)
• NIST Chemistry Reference: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(125664-95-1)
• EPA Substance Registry System: N-PROPIONYL-(2R)-BORNANE- 10,2-SULTAM(125664-95-1)

Safety Data

• Hazardous Substances Data: 125664-95-1(Hazardous Substances Data)

Usage

General Description

N-Propionyl-(2R)-bornane-10,2-sultam is a chemical compound with the molecular formula C13H21NO3S. It belongs to the chemical class of organic compounds known as bicyclic monoterpenoids. These are monoterpenes containing exactly 2 rings, where the oxygen atom is part of a sulfonic acid group. As this chemical is not widely studied, specific information regarding its uses, safety, or environmental impacts is not readily available. Being a relatively complex and specific compound, it is presumably used in specialized fields of chemical research.

Upstream product

• 123-62-6 propionic acid anhydride 
• 94594-90-8 (2R)-bornane-10,2-sultam 
• 125664-99-5 N-<(2R,3S)-3-hydroxy-2-methylbutanoyl>bornane-10,2-sultam 
• 220170-24-1 C₈H₁₄O₃ 
• 79-03-8 propionyl chloride 

Downstream Products

• 201936-46-1 (Z)-(2S,9S,10R)-9-(tert-Butyl-dimethyl-silanyloxy)-10-(tert-butyl-diphenyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-undec-6-en-1-one 
• 125664-98-4 (2R,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 
• 1027311-89-2 (2R,3S)-1-((6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-hydroxy-7-((4-methoxybenzyl)oxy)-2-methylheptan-1-one 
• 1228007-30-4 N-[(2S,3S)-3-hydroxy-5-(4-methoxybenzyloxy)-2-methylpentanoyl]-bornane-10,2-sultam 
• 125665-04-5 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((R)-hydroxy-phenyl-methyl)-butan-1-one 
• 125665-04-5 N-<(2S,3S)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 N-<(2R,3R)-2-(hydroxybenzyl)butanoyl>bornane-10,2-sultam 
• 125665-04-5 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-((S)-hydroxy-phenyl-methyl)-butan-1-one 
• 125665-15-8 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-(4-methoxy-phenyl)-2-methyl-propan-1-one 
• 125685-29-2 (R)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-hexan-1-one 
• 125665-18-1 (R)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-butan-1-one 
• 125665-07-8 N-<(2R,3R)-2-(hydroxybenzyl)hexanoyl>bornane-10,2-sultam 
• 125665-10-3 (2S,3R)-3-((tert-butyldimethylsilyl)oxy)-1-((6R)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-2-methyl-3-phenylpropan-1-one 
• 125760-70-5 (2S,3R)-1-((6R)-8,8-dimethyl-2,2-dioxidotetrahydro-3H-3a,6-methanobenzo[c]isothiazol-1(4H)-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one 

Relevant articles and documents

Stereoselective α-Hydroxylation of Amides Using Oppolzer's Sultam as Chiral Auxiliary

An Oppolzer's sultam-based highly stereoselective α-hydroxylation of amides was developed to deliver the desired products in good yield and excellent diastereoselectivity (>20/1). The generally crystalline products and the recyclability of the chiral auxiliary illustrate the practicability and scalability of the current approach.

Diastereoselective synthesis of the C14-C29 fragment of amphidinol 3

An efficient stereoselective synthesis of the C14-C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, l-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present in the C14-C29 fragment of amphidinol 3.

Synthesis of enantiomerically pure divinyl- and diallylcarbinols

Acylated oxazolidinones and bornane sultams can be cleaved to divinyl- and diallylcarbinols by treatment with vinyl- or allylmetal compounds. For the preparation of divinylcarbinols, acylated bornane sultams are the starting materials of choice, while for the preparation of diallylcarbinols acylated oxazolidinones and bornane sultams work equally well.