69363-09-3

Basic information

• Product Name: (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
• Synonyms: (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol
• CAS NO: 69363-09-3
• Molecular Formula: C₁₀H₁₉NO
• Molecular Weight: 169.26
• Product Categories: Chiral Reagents
• Mol File: 69363-09-3.mol

Chemical Properties

• Boiling Point: 239 ºC
• Flash Point: 99 ºC
• Appearance: /
• Density: 1.015
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol(69363-09-3)
• EPA Substance Registry System: (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol(69363-09-3)

Safety Data

• Hazardous Substances Data: 69363-09-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol is used as a chiral building block for the synthesis of complex organic molecules, particularly in the production of pharmaceuticals. Its unique structure and stereochemistry enable the creation of enantiomerically pure compounds, which are essential for the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (1S,2S,3R,5S)-3-Amino-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol serves as a key intermediate in the synthesis of chiral agrochemicals. Its ability to form enantiomerically pure compounds contributes to the development of more targeted and environmentally friendly pesticides and other agricultural chemicals.

InChI:InChI=1/C10H19NO/c1-9(2)6-4-7(9)10(3,12)8(11)5-6/h6-8,12H,4-5,11H2,1-3H3/t6-,7-,8+,10-/m0/s1

Upstream product

• 80138-53-0 (1S,2S,3R)-2α-hydroxy-3α-(p-toluenesulfonamido)-pinane 
• 67617-36-1 2α-hydroxy-2,6,6-trimethybicyclo<3.1.1>heptan-3-one oxime 
• 7785-70-8 (+)-α-pinene 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 

Downstream Products

• 80138-53-0 (1S,2S,3R)-2α-hydroxy-3α-(p-toluenesulfonamido)-pinane 
• 1337426-46-6 (S)-benzyl 2-((1S,2S,3R,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarbamoyl)-pyrrolidine-1-carboxylate 
• 1563207-96-4 benzyl (S)-N-[((1S,2S,3R,5S)-2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylamino)-3-methyl-1-oxobut-2-yl]carbamate 

Relevant articles and documents

COMPOUNDS, COMPOSITIONS AND METHODS FOR SYNTHESIS

The present disclosure, among other things, provides technologies for synthesis, including reagents and methods for stereoselective synthesis. In some embodiments, the present disclosure provides compounds useful as chiral auxiliaries. In some embodiments, the present disclosure provides reagents and methods for oligonucleotide synthesis. In some embodiments, the present disclosure provides reagents and methods for chirally controlled preparation of oligonucleotides. In some embodiments, technologies of the present disclosure are particularly useful for constructing challenging internucleotidic linkages, providing high yields and stereoselectivity.

New chiral ligands derived from (+) and (-)-α-pinene for the enantioselective addition of diethylzinc to aldehydes

In this study, we synthesized five new chiral ligands from (+) and (-)-α-pinene, which were successfully employed in the stereoselective addition of diethylzinc to aldehydes, leading to secondary chiral alcohols in up to 99% yield and 94% e.e.

A practical method for preparation of optically pure oxazaborolidines from α-pinene

(1S,2S,3R,5S)- and (1S,2S,3R,5S)-3-amino-2-hydroxypinane (1 and 2) were prepared from the corresponding α-pinene in optically pure form. They and their derivatives reacted with various organoborane compounds. A variety of chiral oxazaborolidines 3a-e and 4 were obtained in high yield.

REACTIONS OF UNSATURATED TERPENE COMPOUNDS WITH CHLORAMINE-T. PART I. (1R,2S,4S)-1-HYDROXY-2-(p-TOLUENESULFONAMIDO)-p-MENTHANE AND (1S,2S,3R)-2-HYDROXY-3-(p-TOLUENESULFONAMIDO)-PINANE

Reactions of p-menth-1-ene and α-pinene with chloramine-T in presence of catalytic quantities of OsO4 have been investigated.Homogeneous products were isolated, the structure of which was established on the basis of spectral analyses and chemical transfor