81801-09-4

Upstream product

• 81801-08-3 4-O-benzyl-2,3-O-isopropylidene-aldehydo-D-erythrose 
• 78469-77-9 1-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 19139-73-2 (4S,4’R,5R)-5-[(benzyloxy)methyl]-2,2,2’,2’-tetramethyl-4,4’-bis[1,3-dioxolane] 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 126581-14-4 D-2,3-isopropylidene tartaric acid 
• 346588-20-3 1-O-benzyl-2,3-O-(1-methylethylidene)-D-arabinitol 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 100-39-0 benzyl bromide 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 130145-94-7 (2R,3S,4S,5S,6S,7S)-1,8-Bis-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octane-2,3,6,7-tetraol 
• 130145-94-7 (2R,3S,4S,5S,6S,7R)-1,8-Bis-benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octane-2,3,6,7-tetraol 
• 130145-83-4 C₃₄H₅₄O₄Si₂ 
• 130146-05-3 C₃₄H₅₄O₄Si₂ 

Downstream Products

• 161615-36-7 (4Z,2R,3R)-2,3-O-Isopropylidene-4-pentadecen-1-ol benzyl ether 
• 214400-48-3 (R)-2-[(R)-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 214400-49-4 (R)-2-[(S)-((4R,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 129829-32-9 5-Z-<(2R,3R)-4-benzyloxy-2,3-isopropylidenedioxy>butylidene-3-(4-methoxybenzyl)hydantoin 
• 338385-66-3 (4S)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether 
• 338385-67-4 (4R)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether 
• 850144-19-3 (3R,4R)-1,2-epoxy-3,4-(isopropylidenedioxy)pentan-5-yl benzyl ether 
• 929207-21-6 4-[(5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxan-5-one 
• 929207-23-8 4-[(5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxymethoxy-methyl]-2,2-dimethyl-[1,3]dioxan-5-one 
• 141782-37-8 (2'R,3'R,5Z)-5-(4'-benzyloxy-2',3'-dihydroxybutylidene)-3-(p-methoxybenzyl)hydantoin 
• 141782-43-6 5'-O-benzyl-2'-deoxyhydantocidin 
• 130508-79-1 (5R,7R)-7-Benzyloxymethyl-3-(4-methoxy-benzyl)-6-oxa-1,3-diaza-spiro[4.4]nonane-2,4,8-trione 
• 130607-49-7 5'-O-benzyl-2'-deoxy-3-N-(p-methoxybenzyl)-3'-oxohydantocidin 

Relevant academic research and scientific papers

Stereoselective Synthesis of the C27-C35 Eribulin Fragment and Its Utilization in Building Structurally Diverse Macrocycles

A practical and scalable stereoselective synthesis of the western substituted tetrahydrofuran ring C27-C35 fragment of eribulin was developed by using (2S,3S)-tartaric acid as a cheap starting material that was converted into an intermediate through a stereoselective vinylation and cross-metathesis as the key steps. A regio-and stero-selective intramolecular oxy-Michael cyclization or an iodocyclization reaction finally provided the required western tetrahydrofuran ring fragment and its related isomeric analogues. These key fragments were further utilized in obtaining several types of macrocyclic derivatives for exploration of their biological properties. The simplicity of our present approach has the potential to be considered for large-scale syntheses of key fragments of eribulin and related analogues.

A new stereoselective total synthesis of phomonol

A stereoselective total synthesis of phomonol, following organocatalytic enantioselective epoxidation and intramolecular oxa-Michael reaction as key steps, is described. The use of readily available dtartaric acid as a chiral source renders this approach

Stereoselective addition of Grignard reagents to sulfinimines derived from tartrate diol (threitol): Generation of chiral building blocks for the collective total synthesis of lentiginosine, conhydrine and methyldihydropalustramate

A systematic investigation of the addition of Grignard reagents to sulfinimines derived from tartaric acid diol was undertaken. It was observed that the chirality of the inherent tartrate moiety influences the diastereoselectivity of the resultant sulfinamides formed in the reaction. The formed products serve as excellent building blocks for the synthesis of natural products. This has been demonstrated in the collective total synthesis of lentiginosine, (+)-α-conhydrine and methyldihydropalustramate.

Towards stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A

The stereoselective synthesis of the C(31)-C(39) and C(20)-C(27) fragments of phorboxazole A (1) was achieved from commercially available and inexpensive D-mannitol. Crimmins aldol reaction and a decarboxylative Claisen-type reaction are the key steps for

First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B

The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying

The 1,3-dipolar cycloaddition reaction of chiral carbohydrate-derived nitrone and olefin: Towards long-chain sugars

The thermal and microwave-activated 1,3-dipolar cycloadditions of several α,β-unsaturated esters derived from d-mannose and chiral nitrones derived from threitol have been studied as a model reaction en route to eleven carbon long chain carbohydrates. Ver

First total synthesis and absolute configuration of the styryl lactone gonioheptolide A

Efficient asymmetric syntheses of both naturally occurring and non-naturally occurring enantiomers of gonioheptolide A are reported. The absolute configuration of (+)-gonioheptolide A was established by NOESY, Mosher ester analysis, and comparison with the specific rotation of the isolated (+)-gonioheptolide A. Georg Thieme Verlag Stuttgart.

Synthesis and evaluation of 1-deoxy-D-xylulose 5-phosphoric acid analogues as alternate substrates for methylerythritol phosphate synthase

(Chemical Equation Presented) Four deoxyxylulose phosphate (DXP) analogues were synthesized and evaluated as substrates/ inhibitors for methylerythritol phosphate (MEP) synthase. In analogues CF3-DXP (1), CF 2-DXP (2), and CF-DXP (3)

Synthesis and biological evaluation of new cross-conjugated dienone marine prostanoid analogues

The synthesis of a series of brominated cross-conjugated dienones, marine prostanoid analogues, was considered using two cyclopentannelation processes, from enamine (by a domino 3-aza Claisen/Mannich reaction) and from dioxolane ester alkylation followed by intramolecular Wittig reaction. All the compounds synthesized featured the same cross-conjugated dienone system, with a vicinal syn or anti diol on the ω-chain. The replacement of the ω-side-chain of the natural prostanoids with a 1-hydroxyphenyl-butyl moiety gave new prostanoids (32-34) with good cytotoxicities. In a second series of products, the possibility of a shorter α-side-chain bearing a simple phenyl ester was investigated. The results indicated a dramatic increase in the cytotoxicity (39, 40, 43, 44). Finally, in a third series, the ω- 1-hydroxyphenyl-butyl was replaced by a 1-hydroxymethyloxybenzyl chain. These simpler compounds (45,46,47,48, 60) are still highly cytotoxic, in the medium range of 60 nM, close to the value of natural punaglandins.

A stereoselective synthesis of (+)-boronolide

A stereoselective synthesis of (+)-boronolide is described. The key steps involve a stereoselective reduction of an α-hydroxy ketone, allylation of an α-hydroxy aldehyde and a ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester