152893-54-4

Basic information

• Product Name: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol
• Synonyms: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol;(1,1-DiMethylethyl)[[(2E)-3-iodo-2-butenyl]oxy]diMethyl-silane
• CAS NO: 152893-54-4
• Molecular Formula: C₁₀H₂₁IOSi
• Molecular Weight: 312
• Product Categories: Miscellaneous Reagents
• Mol File: 152893-54-4.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol(152893-54-4)
• EPA Substance Registry System: O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol(152893-54-4)

Safety Data

• Hazardous Substances Data: 152893-54-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol is used as a synthetic reagent for the production of retinoids, which are essential for maintaining proper vision, growth, and immune function. The compound plays a crucial role in the synthesis process due to its unique reactivity and functional groups, contributing to the development of therapeutically relevant molecules.
Used in Chemical Research:
In the field of chemical research, O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol serves as a valuable intermediate for the synthesis of various complex organic molecules. Its unique structure and reactivity make it a versatile building block for creating novel compounds with potential applications in different industries.
Chemical Properties:
O-tert-ButyldiMethylsilyl-3-iodo-(2E)-buten-1-ol is often referred to as "Pink Oil" due to its distinctive color. This characteristic is a result of its chemical composition and electronic structure, which can be useful for identifying the compound during experimental procedures.

Upstream product

• 764-01-2 methyl propargyl alcohol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 37428-58-3 (E)-β-iodocrotyl alcohol 
• 83591-03-1 (but-2-yn-1-yloxy)(tert-butyl)dimethylsilane 

Downstream Products

• 228120-19-2 3-{(1E,3E,7E)-9-[(tert-butyl)dimethylsilyloxy]-3,7-dimethylnona-1,3,7-trien-5-ynyl}-2,4,4-trimethylcyclohex-2-en-1-ol 
• 210700-51-9 ((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane 
• 1354744-19-6 (2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-hydroxy-3-methylpent-2-enyloxy}silane 
• 1354744-20-9 (2E)-tert-butyldimethyl{5-[(4'S)-4'-triethylsilyloxy-2',6',6'-trimethylcyclohexenyl]-4-acetoxy-3-methylpent-2-enyloxy}silane 
• 1354744-22-1 (2E)-tert-butyldimethyl{5-[(4'S)-4'-hydroxy-2',6',6'-trimethylcyclohexenyl]-4-acetoxy-3-methylpent-2-enyloxy}silane 
• 1354744-23-2 (2E)-tert-butyldimethyl{5-[(1'S,2'R,4'S)-4'-p-nitrobenzoxy-1',2'-epoxy-2',6',6'-trimethylcyclohex-1'-yl]-4-acetoxy-3-methylpent-2-enyloxy}silane 
• 228120-20-5 3-{(1E,3E,5Z,7E)-9-[(tert-butyl)dimethylsilyloxy]-3,7-dimethylnona-1,3,5,7-tetraenyl}-2,4,4-trimethylcyclohex-2-en-1-ol 

Relevant articles and documents

Exploration of GGTase-I substrate requirements. Part 2: Synthesis and biochemical analysis of novel saturated geranylgeranyl diphosphate analogs

Protein prenylation is a type of post-translational modification that aids certain proteins in localizing to the plasma member where they activate cell signaling. To better understand the isoprenoid requirements and differences of FTase and GGTase-I, a series of saturated geranylgeranyl diphosphate analogs were synthesized and screened against both mammalian FTase and GGTase-I. Of our library of compounds, several analogs proved to be substrates of GGTase-I, with 11d having a krel?=?0.95 when compared to GGPP (krel?=?1.0).

Metathesis at an Implausible Site: A Formal Total Synthesis of Rhizoxin D

The new approach to the anticancer agent rhizoxin D described herein does not cohere with the conventional logic of metathesis, according to which macrocycles are best closed at a disubstituted olefinic site; rather, the trisubstituted C11?C12 alkene flanked by an allylic -OH group served as the pivot point for synthesis. This motif was attained in good yield and excellent selectivity by a sequence of alkyne metathesis, trans-hydrostannation and cross coupling. Because the exact same substructure is prominently featured in numerous other natural products, the underpinning strategy, though unusual, might bear more general relevance.

Synthesis of the C1-C12 Fragment of Calyculin C

Calyculins are a class of highly cytotoxic metabolites originally isolated from the marine sponge Discodermia calyx. To date, a total of twelve different calyculins (A-J) and calyculinamides (A, B and F) have been described, the most abundant (in D. calyx

Synthesis of an advanced intermediate enroute to thiomarinol antibiotics

A stereoselective synthesis of the C1-C14 fragment of thiomarinols is disclosed. The key steps include the stereoselective preparation of an allylic sulfide via a chloro sulfide by 1,2-asymmetric induction, ring-closing metathesis reaction, Kirmse-Doyle reaction for the preparation of a γ,δ-unsaturated ester, Nozaki-Hiyama-Kishi coupling and Julia-Kocienski olefination reaction. Substrate controlled asymmetric induction has been advantageously employed for the creation of stereogenic centers. Noyori transfer hydrogenation and asymmetric hydrogenation reactions have been utilized for the creation of carbinol stereocenters.

Synthesis of Non-natural, Frame-Shifted Isoprenoid Diphosphate Analogues

A set of synthetic approaches was developed and applied to the synthesis of eight frame-shifted isoprenoid diphosphate analogues. These analogues were designed to increase or decrease the methylene units between the double bonds and/or the pyrophosphate m

Synthesis of frame-shifted farnesyl diphosphate analogs

A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isop

New synthetic methodology for the construction of 7-substituted farnesyl diphosphate analogs

Through the use of a 1,2-metalate rearrangement, six 7-substituted farnesol analogs were generated in a concise manner. This new synthetic route allowed us to quickly prepare several diverse farnesyl diphosphate analogs with interesting biological activit

A convenient and genuine equivalent to HZrCp2Cl generated in situ from ZrCp2Cl2-DIBAL-H

Slow addition of 1 equiv of 1Bu2AlH to ZrCp 2Cl2 in THF provides a convenient route to either HZrCp2Cl-1Bu2AlCl (Reagent I) or HZrCp 2Cl (Reagents II and III). The latter represents a highly convenient route to genuine HZrCp2Cl, while Reagent I is useful for regio- and stereoselective conversion of 1- and 2-alkynes into (E)-1-iodo-1-alkenes and (E)-2-iodo-2-alkenes, respectively.

Efficient synthesis of 11-cis-retinoids

The light sensitivity and unstable nature of 11-cis-retinoids makes them ideal visual chromophores in nature. The synthesis of 11-cis-retinal analogues is of paramount importance in bioorganic studies of rhodopsin, the photoreceptor of the visual transduction pathway, but the instability of 11- cis-retinoids complicates their synthesis and there is no general synthetic route. Common strategies to the cis geometry have failed in the case of 11- cis-retinoids, and most often low yields and complex isomeric mixtures are obtained. Herein we report an efficient, general, and mild preparation of 11- cis-retinoids by semi-hydrogenation of 11-yne-retinoid precursors with Cu/Ag- activated zinc dust.

Nozaki-Kishi reaction of crotonates as a source of complex dienophiles. Application to the B-seco taxane series

The Nozaki-Kishi coupling reaction between aldehyde 10 and 3-iodo-(E)-crotonate derivatives is used to produce functionalized allylic alcohols which served as precursors of highly substituted enones.Diels-Alder reactions of various dienophiles derived fro