142096-80-8

Basic information

• Product Name: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol
• Synonyms: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol
• CAS NO: 142096-80-8
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• Mol File: 142096-80-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol(142096-80-8)
• EPA Substance Registry System: ((1R,2R)-2-(benzyloxyMethyl)cyclopropyl)Methanol(142096-80-8)

Safety Data

• Hazardous Substances Data: 142096-80-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
BOC-Methanol is employed as a building block in the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of complex molecules with specific biological activities.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In asymmetric synthesis reactions, BOC-Methanol serves as a chiral auxiliary, leveraging its stereochemistry to influence the outcome of the reaction. This application is crucial for producing enantiomerically pure compounds, which are essential in many pharmaceutical and chemical applications.
Used as a Protecting Group for Alcohols in Organic Chemistry:
BOC-Methanol can be utilized as a protecting group for alcohols, enabling selective manipulation of different functional groups within a molecule. This selective protection is vital for complex organic synthesis processes, ensuring that specific reactions occur without unwanted side reactions.

Upstream product

• 80885-30-9 (E)-4-(benzyloxy)-2-buten-1-ol 
• 14399-53-2 bis(iodomethyl)zinc 
• 75-11-6 diiodomethane 
• 534584-66-2 (1R,2R)-2-((benzyloxy)methyl)cyclopropanecarbaldehyde 
• 100-39-0 benzyl bromide 
• 154001-59-9 (1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane 
• 58931-16-1 (R)-1-benzyloxypent-4-en-2-ol 
• 14618-80-5 (R)-benzyl glycidol 
• 142176-75-8 (Z)-(R)-1-benzyloxy-6-(trimethyl-silanyl)-hex-4-en-2-ol 
• 188610-46-0 1-((((1R,2S)-2-vinylcyclopropyl)methoxy)methyl)benzene 
• 561055-26-3 (1R,2R)-2-Benzyloxymethyl-cyclopropanecarboxylic acid ethyl ester 
• 52745-75-2 (-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane 
• 100-44-7 benzyl chloride 
• 337983-96-7 Allyl-((R)-1-benzyloxymethyl-but-3-enyloxy)-dimethyl-silane 

Downstream Products

• 1101900-27-9 2-methylsulfonyloxymethylene cyclopropylmethyl benzyl ether 
• 1101900-29-1 2-fluoromethylene cyclopropylmethyl benzyl ether 
• 534584-81-1 (1R,2R)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-[(S)-1-hydroxyethyl]cyclopropane 
• 534585-45-0 (1R,2R)-2-benzyloxymethyl-1-ethanoylcyclopropane 
• 534584-66-2 (1R,2R)-2-((benzyloxy)methyl)cyclopropanecarbaldehyde 
• 52745-75-2 (-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane 

Relevant articles and documents

Ring-conformer effects of the cyclopropyl group: First use of trans-(2r,3r)-cyclopropanecarbaldehydes as electrophiles in diastereoselective baylisihillman reaction

trans-(2R,3R)-Cyclopropanecarbaldehydes are used as novel electrophiles in the Baylis-Hillman reaction to afford adducts in good yields (75-85%) and diastereoselectivities (60-90%).

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.

A systematic study of the hydride reduction of cyclopropyl ketones with structurally simplified substrates. Highly stereoselective reductions of trans-substituted cyclopropyl ketones via the bisected s-cis conformation

The stereoselective hydride reduction of the cis- and trans-substituted cyclopropyl ketones was systematically investigated using a series of structurally simplified substrates, trans-[tertbutyldiphenylsilyloxymethyl]cyclopropyl ketones 1a-e and trans-(benzyloxymethyl)cyclopropyl methyl ketone (2), and the corresponding cis congeners 3a,b,e and 4. The results showed that, not only in the reduction of the cis-substituted cyclopropyl ketones but also in that of the trans-substituted ketones, high stereoselectivity can be realized when the substrate has a bulky substituent on the cyclopropane ring, even though it is attached to the position trans to the acyl moiety. Ab initio calculations based on the density functional theory (DFT) of cyclopropyl ketones showed that (1) the bisected s-cis and s-trans conformers were the only two minimum energy conformers, while the s-cis conformer was more stable than the s-trans and (2) a bulky alkyl group in the acyl moiety and a cis substituent on the cyclopropane ring made the bisected s-cis conformer much more stable. On the basis of these calculations and experimental results, it is likely that the more stable the bisected s-cis conformer of the substrate, the more stereoselective the hydride reduction. Thus, the stereochemistry can be explained by hydride attack on the bisected s-cis conformation of the substrate from the less-hindered face. The predictability of the stereochemical results is predicated on the bisected s-cis transition-state model, which is very important from the viewpoint of synthetic organic chemistry.

Synthetic methodology for the construction of structurally diverse cyclopropanes

Practical and efficient routes for the stereoselective conversion of homoallylic alchols to diastereomerically pure cis-, trans-1,2-disubstituted, and 1,2,3-trisubstituted cyclopropanes have been developed. The routes are highlighted by olefin metathesis

Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications

A very effective chiral controller has been found for the conversion of allylic alcohols into the corresponding enantiomerically enriched cyclopropanes using bis(iodomethyl)zinc. A variety of chiral, nonracemic cyclopropylmethanols could be obtained according to this method. This methodology was extended with success to the cyclopropanation of unconjugated and conjugated polyenes and homoallylic alcohols. The cyclopropanation of allylic carbamates has also been investigated with this system, but it was found that enantioenriched cyclopropylmethylamines are best prepared from enantioenriched cyclopropylmethanols.

A Catalytic Enantioselective Reaction Using a C2-Symmetric Disulfonamide as a Chiral Ligand: Simmons-Smith Cyclopropanation of Allylic Alcohols by the Et2Zn-CH2I2-Disulfonamide System

A catalytic and enantioselective Simmons-Smith cyclopropanation of an allylic alcohol was developed by the reaction of an allylic alcohol with Et2Zn and CH2I2 in the presence of a catalytic amount of chiral disulfonamide 4.