17881-97-9

Basic information

• Product Name: Methanol, (dimethylphenylsilyl)-
• CAS NO: 17881-97-9
• Molecular Formula: C9H14OSi
• Molecular Weight: 166.295
• Mol File: 17881-97-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Methanol, (dimethylphenylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanol, (dimethylphenylsilyl)-(17881-97-9)
• EPA Substance Registry System: Methanol, (dimethylphenylsilyl)-(17881-97-9)

Safety Data

• Hazardous Substances Data: 17881-97-9(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 768-33-2 phenyldimethylsilyl chloride 
• 5584-87-2 (dimethylphenylsilyl)methyl acetate 
• 869218-44-0 (dimethylphenylsilyl)methyl (S,S)-N,N-bis(1-phenylethyl)carbamate 
• 107735-20-6 [(dimethylphenylsilyl)methyl]magnesium chloride 
• 98-83-9 isopropenylbenzene 
• 869218-63-3 (S)-pinanediol (dimethylphenylsilyl)methylboronate 
• 1833-51-8 chloromethyldimethylphenylsilane 
• 869218-53-1 (R,R)-1,2-dicyclohexylethane-1,2-diol {(1S)-[(S,S)-N,N-bis(1-phenylethyl)carbamoyloxy](dimethylphenylsilyl)methyl}boronate 
• 869218-55-3 (R,R)-1,2-dicyclohexylethane-1,2-diol (dimethylphenylsilyl)methylboronate 
• 869218-54-2 (R,R)-1,2-dicyclohexylethane-1,2-diol {(R)-[(S,S)-N,N-bis(1-phenylethyl)carbamoyloxy](dimethylphenylsilyl)methyl}boronate 

Downstream Products

• 125828-04-8 2-(dimethylphenylsilyl)-1,3-dioxolane 
• 128785-03-5 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(dimethyl-phenyl-silanyl)-methoxy]-tetrahydro-pyran-4-yl ester 
• 125828-05-9 2-(dimethylphenylsilyl)-1,3-dioxane 
• 869218-41-7 (dimethylphenylsilyl)methyl N,N-dimethylcarbamate 
• 2702-58-1 methyl 3,5-dinitrobenzoate 
• 106773-51-7 dimethyl(phenyl)silylmethyl 3-phenoxybenzyl ether 
• 1051943-01-1 (dimethyl(phenyl)silyl)methyl triphenylacetate 
• 869218-44-0 (dimethylphenylsilyl)methyl (S,S)-N,N-bis(1-phenylethyl)carbamate 
• 128785-02-4 C₆₅H₆₆O₁₆Si 
• 128785-00-2 ((2S,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxymethoxymethyl)-dimethyl-phenyl-silane 
• 128785-05-7 Dimethyl-phenyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-silane 
• 128784-95-2 Dimethyl-phenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxymethoxymethyl)-silane 
• 128784-99-6 (2S,3S,4S,5R,6R)-4-[(Dimethyl-phenyl-silanyl)-methoxymethoxy]-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-3,5-diol 
• 128805-40-3 [(5R,6S)-5-(1,2-Bis-benzyloxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxymethoxymethyl]-dimethyl-phenyl-silane 

Relevant articles and documents

Chemical Synthesis of [2H]-Ethyl Tosylate and Exploration of Its Crypto-optically Active Character Combining Complementary Spectroscopic Tools

Small chiral molecules are excellent candidates to push the boundaries of enantiodiscrimination analytical techniques. Here is reported the synthesis of two new deuterated chiral probes, (R)- and (S)-[2H]-ethyl tosylate, obtained with high enantiomeric ex

Direct chemical synthesis of chiral methanol of 98% ee and its conversion to [2H1,3H]methyl tosylate and [ 2H1,3H-methyl]methionine

This paper describes the synthesis of chiral methanols [(R)- and (S)-CHDTOH] in a total of 12 steps starting from (chloromethyl) dimethylphenylsilane. The metalated carbamates derived from (dimethylphenylsilyl)methanol and secondary amines were borylated at low temperatures (-78 or -94°C) using borates derived from fert-butyl alcohol and (+)-pinane-2,3-diol or (R,R)-1,2-dicyclohexylethane-1,2-diol to give diastereomeric boronates (dr 1:1 to 5:1). The carbamoyloxy group could be replaced smoothly with inversion of configuration by an isotope of hydrogen using LiAIH(D)4 [or LiBEt3H(D,T)]. If the individual diastereomeric boronates were reduced with LiAID4 and oxidized with H2O2/NaHCO3, monodeuterated (dimethylphenylsilyl)methanols of ee > 98% resulted. The absolute configurations of the boronates were based on a single-crystal X-ray structure analysis. Brook rearrangement of the enantiomers of (dimethylphenylsilyl)-[ 2H1,3H]methanol prepared similarly furnished the chiral methanols which were isolated as 3,5-dinitrobenzoates in 81% and 90% yield, respectively. For determination of the enantiomeric excesses (98%), the methyl groups were transferred to the nitrogen of (S)-2-methylpiperidine and 3H{1H} NMR spectra were recorded. The Brook rearrangement is a stereospecific process following a retentive course. The chiral methanols were also transformed into methyl tosylates used to prepare [2H 1,3H-methyl]methionines in high overall yields (>80%).

Use of (phenyldimethylsilyl)methoxymethyl and (phenyldimethylsilyl)methyl ethers as protecting groups for sugar hydroxyls

The reagent (phenyldimethylsilyl)methoxymethyl chloride (SMOM-Cl) proved to be very convenient for the formation of the corresponding SMOM ethers of primary and secondary hydroxyls of sugars. Further, (phenyldimethylsilyl)methanol (SMOH), the precursor of