103708-37-8

Basic information

• Product Name: 1,3-Dioxane-4-methanol, 2-(4-methoxyphenyl)-, (2S,4S)-
• CAS NO: 103708-37-8
• Molecular Formula: C12H16O4
• Molecular Weight: 224.257
• Mol File: 103708-37-8.mol

Chemical Properties

• CAS DataBase Reference: 1,3-Dioxane-4-methanol, 2-(4-methoxyphenyl)-, (2S,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dioxane-4-methanol, 2-(4-methoxyphenyl)-, (2S,4S)-(103708-37-8)
• EPA Substance Registry System: 1,3-Dioxane-4-methanol, 2-(4-methoxyphenyl)-, (2S,4S)-(103708-37-8)

Safety Data

• Hazardous Substances Data: 103708-37-8(Hazardous Substances Data)

Upstream product

• 42890-76-6 (S)-1,2,4-butanetriol 
• 123-11-5 4-methoxy-benzaldehyde 
• 196861-66-2 (S)-2,2,9,9-tetramethyl-5-<(trimethylsilyl)oxy>-3,8-dioxa-2,9-disiladecane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 

Downstream Products

• 103708-40-3 (S,S)-2-(4-Methoxyphenyl)-4-hexadecyloxymethyl-1,3-dioxane 
• 196861-67-3 Toluene-4-sulfonic acid (2S,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl ester 
• 208586-53-2 (2S,4S)-2-(4-Methoxyphenyl)-1,3-dioxane-4-carbaldehyde 
• 231299-11-9 (2S,4S)-tert-butyl-[2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethoxy]-diphenyl-silane 
• 1460293-50-8 (7S,8S,10S)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-7,8-dihydroxyundecyl pivalate 
• 1460293-51-9 6-((4S,5S)-5-((S)-2-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)-oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)hexyl pivalate 
• 1460293-53-1 C₃₆H₆₄O₇Si 
• 1460293-49-5 (S,E)-10-((4R,5S)-5-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-2,2-dimethyl-1,3-dioxolan-4-yl)undec-7-en-1-yl pivalate 
• 1460293-48-4 (10S,11R,14S,E)-16-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-((4-methoxybenzyl)oxy)-10-methyl-12-oxohexadec-7-en-1-yl pivalate 
• 1460293-59-7 (10S,E)-11-(2-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-1,3-dithian-2-yl)-11-hydroxy-10-methylundec-7-en-1-yl pivalate 
• 1460293-60-0 (10S,E)-11-(2-((S)-4-((tert-butyldimethylsilyl)oxy)-2-((4-methoxybenzyl)oxy)butyl)-1,3-dithian-2-yl)-11-hydroxy-10-methylundec-7-en-1-yl pivalate 
• 1460293-46-2 (S)-4-(1,3-dithian-2-yl)-3-((4-methoxybenzyl)oxy)butan-1-ol 
• 1460293-45-1 (4S)-4-((1,3-dithian-2-yl)methyl)-2-(4-methoxyphenyl)-1,3-dioxane 
• 1460293-44-0 (4S)-4-(iodomethyl)-2-(4-methoxyphenyl)-1,3-dioxane 

Relevant articles and documents

Diastereoselective synthesis of the C14-C29 fragment of amphidinol 3

An efficient stereoselective synthesis of the C14-C29 fragment highlighting a coupling reaction between a 1,3-dithiane derivative and an α-branched aldehyde was realized. This highly convergent synthesis involved two chiral pools, l-malic acid and (+)-camphorsulfonic acid, which are the starting compounds to control the six stereogenic centers present in the C14-C29 fragment of amphidinol 3.

Studies towards the total synthesis of (-)-caulerpenynol, a toxic sesquiterpenoid of the green seaweed caulerpa taxifolia

The first diastereoselective synthesis of the antimicrobial and cytotoxic agent (-)-caulerpenynol (2) was achieved in relatively few steps from, commercially available (S)-malic acid, Highlights of this synthesis include the nonracemization. of the sensitive a-hydroxy ketone moiety and the proper choice of the protecting groups for critical last deprotection step. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

The first total synthesis of (-) and (+)-2-hydroxy-24-oxooctacosanolide using an effective lactonization

(Chemical Equation Presented) An effective method for the total synthesis of 2-hydroxy-24-oxooctacosanolide, a defensive salivary secretion of the African termite Pseudacanthotermes spiniger, has been developed. The key lactonization to form a 29-membered ring lactone core is performed using 2-methyl-6- nitrobenzoic anhydride with a catalytic amount of 4-(dimethylamino)pyridine N-oxide.

Synthesis of 1alpha,25-dihydroxyvitamin D3-26,23-lactams (DLAMs), a novel series of 1 alpha,25-dihydroxyvitamin D3 antagonist.

Novel vitamin D(3) analogs having a lactam structure in their side chains, 1 alpha,25-dihydroxyvitamin D(3)-26,23-lactams (DLAMs), were designed based on the principle of regulation of the folding of helix-12 in the vitamin D nuclear receptor (VDR). The n

Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue

(+)-Loline (1) was synthesized via a pathway that employed intramolecular [4 + 2] cycloaddition of an acylnitrosodiene, 25 or 26, as a key step. The acylnitrosodienes, which were used in situ, were obtained by oxidation of the corresponding hydroxamic acids, 17 and 24, and these were prepared from either glucose via aldehyde 9 or more directly from (S)-malic acid (18). The endo dihydrooxazines 27 and 29, obtained in a mixture with their exo stereoisomer, were transformed by reductive N-O bond cleavage and reannulation into pyrrolizines 34 and 35. The latter was subjected to Sharpless aminohydroxylation in the presence of (DHQD)2PHAL to give 50 along with its regioisomer 51. N-Methylation of tosyl amide 50, followed by mesylation of alcohol 52 and reduction of the γ-lactam 53 with borane, afforded pyrrolizidine 54. Cleavage of the p-methoxybenzyl ether and subsequent thermal treatment of 55 resulted in intramolecular etherification to yield N-tosylloline (57). Final reductive cleavage of the N-tosyl residue produced (+)-loline, characterized as its dihydrochloride.

Toward a total synthesis of pristinamycin II(B); a chiron approach to a C-9/C-16 fragment

Copper(I)-catalysed addition of methyl Grignard reagent to the propagyl diol 8, which was efficiently prepared from S-malic acid proceeds with a perfect E stereoselectivity, the diol titus obtained being then converted into the title fragment by known met

Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-6a which formed respectively in these conditions have been converted efficiently into the title fragments of spiramycin.

AN EFFICIENT AND STEREOCONTROLLED SYNTHESIS OF PLATELET ACTIVATING FACTOR FROM (S)-(-)-MALIC ACID

A stereocontrolled synthesis of C16-PAF (11) from (S)-(-)-malic acid (1), employing regioselective hydrogenolytic cleavage of benzylidene acetal derivatives of (S)-1,2,4-butanetriol (2) with borane-tetrahydrofuran complex, is described.