408348-30-1

Basic information

• Product Name: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane
• Synonyms: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane
• CAS NO: 408348-30-1
• Molecular Weight: 480.7
• Mol File: 408348-30-1.mol

Chemical Properties

• CAS DataBase Reference: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane(408348-30-1)
• EPA Substance Registry System: (1R,2S)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethyl-1-phenylsulfonylcyclopropane(408348-30-1)

Safety Data

• Hazardous Substances Data: 408348-30-1(Hazardous Substances Data)

Upstream product

• 408348-28-7 (1R,5S)-1-(phenylsulfonyl)-3-oxabicyclo[3.1.0]hexan-2-one 
• 7605-28-9 2-(phenylsulfonyl)acetonitrile 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 408348-29-8 (1R,2S)-1,2-bis(hydroxymethyl)-1-phenylsulfonylcyclopropane 

Downstream Products

• 408348-31-2 (1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane 
• 154001-59-9 (1R,2R)-2-<<(tert-Butyldiphenylsilyl)oxy>methyl>-1-(hydroxymethyl)cyclopropane 
• 145920-52-1 (1S,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-hydroxymethylcyclopropane 

Relevant articles and documents

Enantioselective total synthesis of (-)-Clavosolide A and B

Enantioselective total synthesis of (-)-clavosolide A and B was reported in full including the synthesis of proposed structure of (-)-clavosoldie A (1), revised structure of (-)-clavosoldie A (5), and revised structure of (-)-clavosoldie B (6). The relative and absolute stereochemistries of the natural products were confirmed unambiguously by comparing the optical rotation values and 1H and 13C NMR spectra of them.

Development of versatile cis- and trans-dicarbon-substituted chiral cyclopropane units: Synthesis of (1S,2R)- and (1R,2R)-2-aminomethyl-1-(1H-imidazol-4-yl)cyclopropanes and their enantiomers as conformationally restricted analogues of histamine

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.