105859-45-8

Basic information

• Product Name: (2S)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-2-METHYLPROPAN-1-OL
• Synonyms: (2S)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-2-METHYLPROPAN-1-OL;(2S)-3-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-2-Methyl-1-propanol
• CAS NO: 105859-45-8
• Molecular Formula: C₁₀H₂₄O₂Si
• Molecular Weight: 204.38
• Product Categories: Chiral Reagents
• Mol File: 105859-45-8.mol
• Article Data: 54

Chemical Properties

• Boiling Point: 232.222°C at 760 mmHg
• Flash Point: 94.245°C
• Appearance: /
• Density: 0.875g/cm³
• Vapor Pressure: 0.011mmHg at 25°C
• Refractive Index: 1.43
• Storage Temp.: -20°C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Dichloromethane (Sparingly), Eth
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: (2S)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-2-METHYLPROPAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-2-METHYLPROPAN-1-OL(105859-45-8)
• EPA Substance Registry System: (2S)-3-([TERT-BUTYL(DIMETHYL)SILYL]OXY)-2-METHYLPROPAN-1-OL(105859-45-8)

Safety Data

• Hazardous Substances Data: 105859-45-8(Hazardous Substances Data)

Usage

Chemical Properties

Slightly Yellow Oil

InChI:InChI=1/C10H24O2Si/c1-9(7-11)8-12-13(5,6)10(2,3)4/h9,11H,7-8H2,1-6H3/t9-/m0/s1

Upstream product

• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 288-32-4 1H-imidazole 
• 80657-57-4 3-hydroxy-(2S)-methylpropionate 
• 144-55-8 sodium hydrogencarbonate 
• 304-59-6 Rochelle's salt 
• 201230-82-2 carbon monoxide 
• 85807-85-8 Allyloxy-tert-butyl-dimethyl-silane 
• 2163-42-0 2-methyl-1.3-propanediol 
• 75-24-1 trimethylaluminum 
• 114736-21-9 (E)-(2S,5S)-1-(tert-Butyl-dimethyl-silanyloxy)-2,5,9-trimethyl-deca-3,8-dien-5-ol 
• 125244-91-9 3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-methylpropan-1-ol 
• 122778-41-0 (1R,3R,4S)-p-menthan-3-yl (2R)-3-(dimethyl-t-butylsiloxy-2-methyl)propionate 
• 105859-44-7 methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate 

Downstream Products

• 299430-30-1 (2R)-toluene-4-sulfonic acid 3-(tert-butyldimethylsilanyloxy)-2-methylpropyl ester 
• 122805-19-0 (2S)-3-(dimethyl-t-butylsiloxy)-2-methylpropyl (S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate 
• 1283713-47-2 (S,E)-(7-(4-methoxybenzyloxy)-2,3-dimethylhept-3-enyloxy)(tert-butyl)dimethylsilane 
• 1191041-40-3 C₂₃H₄₁NO₃Si 

Relevant articles and documents

STEREOSELECTIVE SN2' ADDITIONS TO CHIRAL ACYCLIC VINYLOXIRANES

Additions of LiMe2Cu to acyclic vinyloxiranes 4, 5, 6 and 7 proceed predominately anti SN2' to afford the (E)-allylic alcohol products.

Ambruticins: tetrahydropyran ring formation and total synthesis

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Laingolide A and diastereoisomer and synthetic method thereof

The invention belongs to the technical field of synthesis, and particularly relates to a synthesis method of Laingolide A and a diastereoisomer thereof, which comprises the following steps: preparinga compound 8 or ent-8; preparing a compound 15 or 18; carrying out Julia olefination reaction on the compound 8 or ent-8 and a compound 15 or 18 to obtain a compound A; carrying out reductive hydrogenation treatment on the compound A to obtain a compound B; carrying out oxidation treatment on the compound B to obtain a compound C; carrying out amido bond assembly on the compound C and then carrying out esterification reaction to obtain a compound D; and carrying out olefin metathesis reaction on the compound D, and then carrying out olefin isomerization reaction to obtain the Laingolide A or the diastereoisomer thereof. The synthesis method provided by the embodiment of the invention is clear in route and high in synthesis efficiency, and is beneficial to the research on the biological activity of the Laingolide A and the diastereoisomer.