103773-79-1

Upstream product

• 42890-76-6 (S)-1,2,4-butanetriol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 100-52-7 benzaldehyde 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 196861-66-2 (S)-2,2,9,9-tetramethyl-5-<(trimethylsilyl)oxy>-3,8-dioxa-2,9-disiladecane 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 3969-69-5 (+/-)-cis-4-hydroxymethyl-2-phenyl-1,3-dioxolane 
• 153944-89-9 (2S,4S)-(-)-Methyl-2-phenyl-1,3-dioxan-4-carboxylat 
• 153944-94-6 (2S,4S)-(+)-N,N-Dimethyl-2-phenyl-1,3-dioxan-4-carboxamid 

Downstream Products

• 103708-38-9 (S,S)-2-Phenyl-4-hexadecyloxymethyl-1,3-dioxane 
• 130272-62-7 (2S,4S)-4-(methoxymethyl)-2-phenyl-1,3-dioxan 
• 223382-82-9 (2S,4S)-4-<(t-butyldimethylsilyl)oxy>methyl-2-phenyl-1,3-dioxan 
• 548458-28-2 (2S,4S)-benzyl[2-phenyl-(1,3-dioxan-4-yl)methylen]amine 
• 548458-30-6 (1R,2'S,4'S)-1-benzyl-3-methoxy-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole 
• 548458-36-2 (2R,2'S,4'S)-1-tert-butoxycarbonyl-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidin-3-one 
• 548458-29-3 (1R,2'S,4'S)-benzyl[2-methoxy-1-(2-phenyl-1,3-dioxan-4-yl)buta-2,3-dienyl]amine 
• 548458-38-4 (2S,3R,2'S,4'S)-1-tert-butoxycarbonyl-3-hydroxy-2-(2-phenyl-1,3-dioxan-4-yl)pyrrolidine 
• 548458-33-9 (2R,2'S,4'S)-1-benzyl-3-benzyloxy-2-(2-phenyl-1,3-dioxan-4-yl)-2,5-dihydro-1H-pyrrole 
• 1251751-70-8 (2S,4S)-2-phenyl-4-((E)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-1,3-dioxane 
• 164577-87-1 ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-enoate 
• 164471-44-7 ethyl E-3-<(2S,4S)-2-phenyl-1,3-dioxan-4-yl>prop-2-en-ol 
• 140210-14-6 (R,R)-4-(Acetoxymethyl)-2-phenyl-1,3-dioxane 

Relevant academic research and scientific papers

Preparation of (2R,4S)/(2S,4S)-4-hydroxypipecolinic acid derivatives from L-(-)-malic acid

Synthetically important 4-hydroxypipecolinic acid derivatives were efficiently prepared from commercially available L-(-)-malic acid. The stereochemistries of the derivatives synthesized by our method were determined by coupling constant analyses with key methine protons on C2 and C4.

Synthesis of a Cn-Cn+6 building block common to important polyol,polyene antibiotics from a divinylcarbinol by a desymmetrizing sharpless epoxidation

A stereocontrolled synthesis of the enantiomerically pure epoxide 7b from propargyl ether 15 has been realized in 15 steps. Epoxide 7b represents a building block for the "eastern" moieties of the title compounds. Key steps in our approach were a desymmetrizing Sharpless epoxidation (→a€‰anti,cis-16), the selective processing of the bis-enolate of the bis(tert-butyl alkoxyacetate) 11 through a diastereoselective [2,3]-Wittig rearrangement (→a€‰syn,syn-9), and a stereo- and chemoselective iodolactonization (→a€‰35). The CO2H groups of dicarboxylic acid 37 were differentiated in a one-pot bis-oxidation reaction. The latter entailed the novel transformation of HO2CCH2-O-alkyl into AcOCH2-O-alkyl. The termini of a bis(tert-butyl alkoxyacetate) have been differentiated by forming the bis-enolate and engaging one enolate in a diastereoselective [2,3]-Wittig rearrangement. A diastereo- and chemoselective iodolactonization established the stereocenter of the epoxide ring. Copyright

Transacetalization of acetals with butane-1,2,4-triol using cobalt(II) chloride and chlorotrimethylsilane

Transacetalization of acetals with butane-1,2,4-triol was carried out using cobalt(II) chloride and chlorotrimethylsilane as catalysts. The reaction occurs under mild conditions in acetonitrile and with a short reaction time. The synergic effect of the two Lewis acids catalyzes the conversion of butane-1,2,4-triol into (2-alkyl- or 2-aryl-1,3-dioxan-4-yl)methanol derivatives with high regiospecificity and diasteroselectivity. Georg Thieme Verlag Stuttgart · New York.

Biochemistry-Guided Prediction of the Absolute Configuration of Fungal Reduced Polyketides

Highly reducing polyketide synthases (HR-PKSs) produce structurally diverse polyketides (PKs). The PK diversity is constructed by a variety of factors, including the β-keto processing, chain length, methylation pattern, and relative and absolute configurations of the substituents. We examined the stereochemical course of the PK processing for the synthesis of polyhydroxy PKs such as phialotides, phomenoic acid, and ACR-toxin. Heterologous expression of a HR-PKS gene, a trans-acting enoylreductase gene, and a truncated non-ribosomal peptide synthetase gene resulted in the formation of a linear PK with multiple stereogenic centers. The absolute configurations of the stereogenic centers were determined by chemical degradation followed by comparison of the degradation products with synthetic standards. A stereochemical rule was proposed to explain the absolute configurations of other reduced PKs and highlights an error in the absolute configurations of a reported structure. The present work demonstrates that focused functional analysis of functionally related HR-PKSs leads to a better understanding of the stereochemical course.

Total Synthesis and Biological Evaluation of Siladenoserinol A and its Analogues

The total synthesis of siladenoserinol A, an inhibitor of the p53–Hdm2 interaction, has been achieved. AuCl3-catalyzed hydroalkoxylation of an alkynoate derivative smoothly and regioselectively proceeded to afford a bicycloketal in excellent yield. A glycerophosphocholine moiety was successfully introduced through the Horner–Wadsworth–Emmons reaction using an originally developed phosphonoacetate derivative. Finally, removal of the acid-labile protecting groups, followed by regioselective sulfamate formation of the serinol moiety afforded the desired siladenoserinol A, and benzoyl and desulfamated analogues were also successfully synthesized. Biological evaluation showed that the sulfamate is essential for biological activity, and modification of the acyl group on the bicycloketal can improve the inhibitory activity against the p53–Hdm2 interaction.

Improved synthesis of C8-C20 segment of pectenotoxin-2

The C8-C20 segment of pectenotoxin-2 was efficiently synthesized in 16% overall yield in 22 steps from l-malic acid via an improved route.

A new synthetic strategy for 2-deoxy-D-ribose via palladium(II)-catalyzed cyclization of aldehyde

We achieved a total synthesis of 2-deoxy-D-ribose through intramolecular Pd(II)-catalyzed cyclization of aldehyde via an unstable hemiacetal intermediate as a key step. The Japan Institute of Heterocyclic Chemistry.

Third-generation immucillins: Syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase

ImmH (1) and DADMe-ImmH (2) are potent inhibitors of human purine nucleoside phoshorylase (PNP), developed by us and currently in clinical trials for the treatment of a variety of T-cell related diseases. Compounds 1 and 2 were used as templates for the design and synthesis of a series of acyclic immucillin analogues (8-38) in order to identify simplified alternatives to 1 and 2. SerMe-ImmG (8) and DATMe- ImmG (9) displayed the lowest inhibition constants of 2.1 and 3.4 pM, respectively, vs PNP. It was postulated that the flexible natures of 8 and 9 enabled them to adopt conformations resembling those of 1 and 2 within the active site of PNP and that the positioning of two hydroxyl groups was critical for picomolar activity. SerMe-ImmH (10, K d = 5.2 pM) was shown to be orally available in mice with a long biological residence time on blood PNP.

New and concise approach to (R)-α-lipoic acid

A concise enantiospecific synthesis of (S)-6,8-bis(methylsulfonyloxy)- octanoic acid (2), a ready precursor of (R)-(+)-α-lipoic acid (1), is reported. The key step of the synthesis is the coupling of the tosylate derived from (R)-malic acid with phenylpro

Stereoselective total synthesis of the nonenolide (+)-microcarpalide

The enantiomer [(+)-1] of the nonenolide natural product microcarpalide [(-)-1] has been prepared from (S)-malic acid (3) and 3-decyn-1-ol (11) via a sixteen step sequence involving, inter alia, two metathesis processes.