251444-03-8

Basic information

• Product Name: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane
• Synonyms: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane
• CAS NO: 251444-03-8
• Molecular Weight: 338.522
• Mol File: 251444-03-8.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane(251444-03-8)
• EPA Substance Registry System: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane(251444-03-8)

Safety Data

• Hazardous Substances Data: 251444-03-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane serves as a versatile building block for the preparation of complex organic molecules. Its presence in organic synthesis is attributed to its ability to be transformed into a variety of other organic compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane is used as an intermediate in the synthesis of new drugs. Its formyl group makes it a potential precursor for the production of alcohols, aldehydes, and carboxylic acids, which are essential components in medicinal chemistry.
Used in Agrochemical Production:
Similarly, in agrochemicals, (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane is utilized as a key intermediate for synthesizing various agrochemical compounds, contributing to the development of new pesticides and other agricultural products.
Used in Material Science:
(1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane also finds application in material science, where it can be used to develop new materials with specific properties, such as polymers and other advanced materials for various industrial applications.

Upstream product

• 133494-58-3 (1S,2R)-1-<methyl>-2-(hydroxymethyl)cyclopropane 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 154001-53-3 (1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene 
• 409307-02-4 (1S,5R)-2-oxo-1-phenylsulfonyl-3-oxabicyclo[3.1.0]hexane 
• 89395-28-8 (1R,5S)-3-oxabicyclo[3.1.0]hexan-2-one 
• 910630-48-7 (1R,2S)-cis-2-(tert-butyldiphenylsilyloxymethyl)-N-methoxy-N-methyl-1-cyclopropanecarboxamide 
• 153861-48-4 (1R,2S,4'S)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropane 
• 183745-99-5 (1S,2S)-1,2-Bis-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-ethane-1,2-diol 
• 185994-16-5 (S)-1-[(1R,2S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-ethane-1,2-diol 
• 183745-93-9 (4S,5S)-4,5-Bis-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-2,2-dimethyl-[1,3]dioxolane 

Downstream Products

• 185994-17-6 tert-Butyl-diphenyl-((1S,2S)-2-vinyl-cyclopropylmethoxy)-silane 
• 1447825-86-6 C₃₂H₃₉NO₄Si 
• 1447825-85-5 C₃₂H₃₉NO₄Si 
• 1447825-83-3 C₃₂H₃₉NO₄Si 
• 1447825-78-6 C₃₀H₃₃NO₃ 
• 1447825-76-4 C₂₃H₃₀O₂Si 
• 1447825-69-5 C₃₃H₃₉NO₄Si 
• 1447825-67-3 C₃₂H₃₇NO₄Si 
• 1447826-00-7 C₃₀H₃₁NO₄ 

Relevant articles and documents

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The cyclopropane ring can be used effectively in restricting the conformation of biologically active compounds to improve activity and also to investigate bioactive conformations. We designed (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes (1 and 2, respectively) and their enantiomers (ent-1 and ent-2) as conformationally restricted analogues of histamine. The four types of chiral cyclopropanes bearing two differentially functionalized carbon substituents in a cis or trans relationship on a cyclopropane ring, (1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formyl-cyclopropane (7) and (1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane (8) and their enantiomers (ent-7 and ent-8), were developed as the key intermediates for synthesizing 1, 2, ent-1, and ent-2. The reaction between (R)-epichlorohydrin [(R)-12] and phenylsulfonylacetonitrile (13a) in the presence of NaOEt in EtOH followed by treatment with acid gave the chiral cyclopropane lactone 11a with 98% ee in 82% yield. Compound 11a was converted into both the cis- and transchiral cyclopropane units 7 and 8, respectively, via reductive desulfonylation with Mg/MeOH as the key step. The corresponding enantiomers, the cis-substituted ent-7 and the trans-substituted ent-8, were also prepared starting from (S)-epichlorohydrin [(S)-12]. The four conformationally restricted target histamine analogues 1, 2, ent-1, and ent-2 were successfully synthesized from 7, 8, ent-7, and ent-8, respectively. The chiral cyclopropane units 7, 8, ent-7, and ent-8 should be useful as versatile intermediates for synthesizing various compounds having an asymmetric cyclopropane structure.

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