5754-27-8

Upstream product

• 3969-84-4 3,4-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 
• 67-64-1 acetone 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 
• 4239-88-7 O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-D-glucitol 
• 288261-48-3 1,2-3,4-5,6-tri-O-isopropylidene-L-iditol 
• 38145-93-6 (S)-1-((4R,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethane-1,2-diol 
• 38145-93-6 2,3,4,5-di-O-isopropylidene D-glucitol 
• 3969-59-3 mannitol triacetonide 
• 94925-98-1 3,4-O-methylethylidene-D-mannitol 
• 33493-69-5 (1R,1'R)-1,1'-[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]diethane-1,2-diol 

Downstream Products

• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 1217890-90-8 (4R,5R)-4,5-diethynyl-2,2-dimethyl-[1,3]dioxolane 

Relevant academic research and scientific papers

A C2-symmetric pool based flexible strategy: An enantioconvergent synthesis of (+)-valiolamine and (+)-valienamine

A new enantioconvergent strategy directed toward the synthesis of glucosidase inhibitors was developed by using a C2-symmetric element within the chiral pool and by applying an iodine-promoted cyclization of an unsaturated carbonimidothioate for the regio- and diastereocontrolled installation of amino and hydroxy units. Not only does this simple flexible strategy provide a convergent concise approach to (+)-valiolamine (1), but it can also be readily adopted for the synthesis of (+)-valienamine (2). Commercially available and cheap C2-symmetric D-tartaric acid served as the chiral building block. Copyright

A total synthesis of aliskiren

A total synthesis of aliskiren (20) was accomplished. A key in our synthesis was to use the symmetric trans-cisoid-trans-bis-lactone 1 as a precursor. It was expediently prepared by three different routes (Scheme 2). Appending the end groups and functional group transformations completed the synthesis (Scheme 3). Copyright

The enantioselective total synthesis of nemotin

The allene-diyne natural product nemotin was synthesized for the first time through an enantioselective route with the stereogenic center at the lactone moiety derived from l-glutamic acid and the allene axis constructed from the corresponding propargylic

An improved two-step synthetic route to primary allylic alcohols from aldehydes

An improved two-step synthetic route to allylic alcohols from aldehydes has been developed. A modification of the HWE reaction in H2O-2-PrOH (1 : 1) and a convenient protocol to prepare AlH3 in THF from LiAlH 4 and n-BuBr are the key factors in the improvement.

Concise synthesis of iminocyclitols via petasis-type aminocyclization

(Chemical Equation Presented) A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60percent yields by using Petasis-type condensation. The method is very generaland operationally simple, affording a s

Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines

We report herein a general method for the synthesis of new types of chiral acyclic nucleoside four-carbon bisphosphonates. The alkylation of 2-amino-6-chloropurine and adenine was performed with (2S,3S)- or (2R,3R)-1,4-[bis(diisopropoxyphosphoryl)methoxy]]-3-[(methylsulfonyl)oxy]butan-2-yl benzoate. Alkylations provided (2R,3R) or (2S,3S) N9-substituted nucleobases, which were further converted to other derivatives. These conversions included either a modification of the nucleobase or transformation of the bisphosphonate chain. Subsequent deprotection of the diisopropyl esters with bromotrimethylsilane provided the resulting (2R,3R)- or (2S,3S)-bisphosphonic acids.

New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination

New chiral phospholanes 6 were prepared in both enantiomeric forms starting from l- and d-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method wa

Stereodivergent syntheses of highly substituted enantiopure 4-alkoxy-3,6-dihydro-2H-1,2-oxazines by addition of lithiated alkoxyallenes to carbohydrate-derived aldonitrones

Additions of lithiated alkoxyallenes to D-glyceraldehyde-based nitrones 1 and 2 did not provide the expected hydroxylamine derivatives. Instead, a novel [3+3] cyclization process furnished 4-alkoxy-3,6-dihydro-2H-1,2-oxazines 9-14 with excellent syn selectivities and in moderate to good yields. Through precomplexation of the nitrones the corresponding anti-configured 1,2-oxazines 9, 10 and 13 could be obtained with high stereoselectivity. The reactions of nitrones 3-6, derived from D-erythrose or D-threose, generally proceeded less diastereoselectively, but reasonable yields of anti-configured 1,2-oxazines such as anti-17 and anti-19 could be obtained under Lewis acid promotion conditions. This was also the case for reactions of the D-arabinose-derived nitrone 7, which provided the anti-1,2-oxazines 23 and 24 with excellent diastereoselectivity and in good yields. Bisnitrone 8 and lithiated methoxyallene furnished a mixture of six compounds, among which the major component was the C2-symmetric syn/syn-1,2-oxazine 29. The diastereoselectivities of these reactions are interpreted on the basis of Dondoni's model for reactions between organolithium compounds and nitrones. The mechanisms for formation of 1,2-oxazines and of side products are discussed. The method introduced here seems to be of broad applicability and an excellent tool for diastereoselective chain elongation of carbohydrate derivatives, affording stereodefined precursors of aminopolyols and other highly functionalized compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Stereoselective synthesis of (+)-boronolide and its 8-epimer

The synthesis of (+)-boronolide and its 8-epimer utilizing diastereoselective propargylation of α-hydroxy aldehyde was analyzed. The synthesis process was started with D-tertaric acid converted to diethyl (2S, 3S)-2,3-O-isopropylidenetartrate. A method was established with DIBAL-H as the reducing agent at -78°C to reduce esters directly to aldehydes. Diastereoselective propargylation was shown to be used in the synthesis of structurally diverse compounds.

Synthesis and applications of chiral bis-THF in asymmetric synthesis

The synthesis of enantiopure bis-THF is described, starting from d-mannitol. Bis-THF is used as chiral ligand for organolithium reagents in four different reactions. The enantioselectivity provided by this ligand is moderate, and the asymmetric induction is in line with the expected model. Graphical Abstract.