130404-34-1Relevant academic research and scientific papers
Sulfonate protecting groups. Regioselective sulfonylation of myo-inositol orthoesters-improved synthesis of precursors of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate, myo-inositol 1,3,4,5,6-pentakisphosphate and related derivatives.
Sureshan, Kana M,Shashidhar, Mysore S,Praveen, Thoniyot,Gonnade, Rajesh G,Bhadbhade, Mohan M
, p. 2399 - 2410 (2007/10/03)
The regioselectivity of sulfonylation of myo-inositol orthoesters was controlled by the use of different bases to obtain the desired sulfonate. Monosulfonylation of myo-inositol orthoesters in the presence of one equivalent of sodium hydride or triethylamine resulted in the sulfonylation of the 4-hydroxyl group. The use of pyridine as a base for the same reaction resulted in sulfonylation of the 2-hydroxyl group. Disulfonylation of these orthoesters in the presence of excess sodium hydride yielded the 4,6-di-O-sulfonylated orthoesters. However, the use of triethylamine or pyridine instead of sodium hydride yielded the 2,4-di-O-sulfonylated orthoester. Sulfonylated derivatives of myo-inositol orthoesters were stable to conditions of O-alkylation but were cleaved using magnesium/methanol or sodium methoxide in methanol to regenerate the corresponding myo-inositol orthoester derivative. These new methods of protection-deprotection have been used: (i) for the efficient synthesis of enantiomers of 2,4-di-O-benzyl-myo-inositol, which are precursors for the synthesis of D- and L-myo-inositol 1,3,4,5-tetrakisphosphate; (ii) for the preparation of 2-O-benzyl-myo-inositol which is a precursor for the preparation of myo-inositol 1,3,4,5,6-pentakisphosphate.
Sulfonate protecting groups. Regioselective O-sulfonylation of myo-inositol orthoesters
Sureshan, Kana M.,Shashidhar, Mysore S.
, p. 3037 - 3039 (2007/10/03)
Sulfonylation of myo-inositol 1,3,5-orthoesters with alkyl or aryl sulfonyl chlorides in the presence of sodium hydride gives the corresponding 4,6-di-O-sulfonates in good yields. These sulfonates can be cleaved with magnesium in methanol to generate the free myo-inositol derivative. This methodology was used for the preparation of racemic 2,4-di-O-benzyl-myo-inositol and 2-O-benzyl-myo-inositol, which are precursors for some phosphoinositols.
Chemo-enzymatic synthesis of both enantiomers of myo-inositol 1,3,4,5-tetrakisphosphate
Laumen, Kurt,Ghisalba, Oreste
, p. 1374 - 1377 (2007/10/03)
D-Ins(1,3,4,5)P4 and unnatural L-Ins(1,3,4,5)P4 were prepared in gram-quantities from D- and L-2,6-di-O-benzyl-myo-inositol by a chemical phosphorylation and deprotection step in high yield and purity without extensive purification.
The preparation of racemic and enantiomerically pure myo-inositol derivatives as intermediates for the synthesis of phosphatidylinositol 3-, 3,4-bis-, and 3,4,5-tris-phosphates and for the synthesis of analogues of 1D-myo-inositol 1,3,4,5-tetrakisphosphat
Desai, Trupti,Gigg, Jill,Gigg, Roy,Martin-Zamora, Eloisa
, p. 97 - 133 (2007/10/03)
Details of the products obtained by the tin-mediated allylation and benzylation of 1,2-O-isopropylidene-myo-inositol, which were previously described in a preliminary communication, are provided here. Some of the products from these reactions, particularl
The preparation and phosphorylation of 2,5- and 1D-2,6-di-O-benzyl-myo-inositol
Desai,Gigg,Gigg,Payne
, p. 65 - 79 (2007/10/02)
1,3,4,6-Tetra-O-allyl-myo-inositol was converted into the 2,5-di-O-benzyl- and 2,5-di-O-p-methoxybenzyl ethers, and the products were deallylated to give the 2,5-di-O-benzyl (and p-methoxybenzyl) ethers of myo-inositol, which were converted into the mono-
The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate
Billington, David C.,Baker, Raymond,Kulagowski, Janusz J.,Mawer, Ian M.,Vacca, Joseph P.,et al.
, p. 1423 - 1429 (2007/10/02)
Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).
