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(3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(para-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone is a complex organic compound with a molecular formula of C19H32O8SSi. It is a chiral molecule, meaning it has a non-superimposable mirror image, with the R and S configurations at the 3rd and 5th carbon atoms, respectively. The compound features a tert-butyldimethylsilyl (TBDMS) group at the 3-hydroxyl position, which is a protecting group commonly used in organic synthesis to shield hydroxyl groups from unwanted reactions. Additionally, it has a para-tolylsulfonyl (p-Ts) group at the 6-hydroxyl position, which serves as a leaving group or a protecting group for the hydroxyl group. The δ-lactone structure indicates the presence of a cyclic ester formed between the 5-hydroxyl group and the carboxylic acid group. (3R,5S)-3-O-(tert-butyldimethylsilyl)-6-(para-tolylsulfonyl)-3,5,6-trihydroxyhexanoic acid δ-lactone is typically used as an intermediate in the synthesis of more complex organic molecules, particularly in the field of natural product chemistry and pharmaceuticals, due to its unique protecting group combinations and chiral centers.

91312-59-3

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91312-59-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 91312-59-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,3,1 and 2 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 91312-59:
(7*9)+(6*1)+(5*3)+(4*1)+(3*2)+(2*5)+(1*9)=113
113 % 10 = 3
So 91312-59-3 is a valid CAS Registry Number.

91312-59-3Downstream Products

91312-59-3Relevant academic research and scientific papers

Method for the production of statins

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, (2008/06/13)

According to the invention, a process for the preparation of a statin is provided, comprising the following steps: a) preparation of a compound of the formula II in which S1 denotes a hydrogen atom or a hydroxylprotective group, S2 and S3, independently of one another, denote hydroxylprotective groups and R1 represents a hydrogen atom or a carboxylprotective group, by stereoselective hydrogenation of a compound of the formula III to give a compound of the formula II-a and optionally introduction of a hydroxylprotective group and b) lactonization of the compound of the formula II to give a compound of the formula I-a

Synthesis of the chiral side chain of statins - Lactone versus lactol pathway

Tararov, Vitali I.,Andrushko, Natalia,Andrushko, Vasyl,Koenig, Gerd,Spannenberg, Anke,Boerner, Armin

, p. 5543 - 5550 (2008/02/04)

4-O-Protected (4R,6S)-4-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-ones (3) derived from enantiomerically pure (3R,5S)-3-hydroxy-5,6-(isopropylidenedioxy) hexanoates (2) are frequently considered as pivotal intermediates for the synthesis of pharmacologic

METHOD FOR THE PRODUCTION OF STATINS

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Page/Page column 24; 28, (2010/11/24)

The invention relates to a method for producing statins known as HMG-CoA reductase inhibitors. Some of the intermediate compounds used in the inventive method are novel compounds. The invention also relates to said novel intermediate compounds.

METHOD FOR THE PRODUCTION OF STATINS

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Page/Page column 29, (2010/02/11)

The invention relates to a method for the production of a statin. Said method comprises the following steps: a) a compound of formula (II) is produced, wherein S1 represents a hydrogen atom or a hydroxyl protective group, S2 and S3 independently represent a hydroxyl protective group and R1 represents a hydrogen atom or a carboxyl protective group. Said compound of formula (II) is produced by stereoselective hydrogenation of a compound of formula (III) in order to form a compound of formula (II-a) and, optionally, by introducing a hydroxyl protective group. b) by lactonising the compound of formula II in order to form a compound of formula (I-a).

Bakers' yeast oxidation of methyl para-tolylsulfide: Synthesis of a chiral intermediate in the preparation of the mevinic acid-type hypocholestemic agents

Tang, Jenny,Brackenridge, Ian,Roberts, Stanley M.,Beecher, Jean,Willetts, Andrew J.

, p. 13217 - 13238 (2007/10/02)

The use of (R)-methyl-para-tolylsulfoxide as a chiral auxiliary in a novel synthesis of a key intermediate en route to mevinic acid-type hypocholestemic agents is described. The synthesis is short and simple consisting of eight steps to yield enantiomeric

Oxidation of methyl p-tolyl sulfide with backers' yeast: preparation of a synthon of the mevinic acid-type hypocholestemic agents

Beecher, Jean,Brackenridge, Ian,Roberts, Stanley M.,Tang, Jenny,Willetts, Andrew J.

, p. 1641 - 1644 (2007/10/02)

Bakers' yeast oxidized methyl p-tolyl sulfide to produce the R-sulfoxide 1 in good yield and high enantiomeric excess; the sulfoxide 1 was used to prepare (4R,6S)-tert-butyldimethylsilyloxy-6-hydroxymethyltetrahydropyran-2-one 15.

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