850166-83-5

Upstream product

• 409064-73-9 C₁₂H₁₆O₃ 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 119649-27-3 4-((4-methoxybenzyl)oxy)butanal 
• 2746-25-0 p-Methoxybenzyl bromide 
• 119649-45-5 4-(p-methoxybenzyloxy)butan-1-ol 
• 824-94-2 p-methoxybenzyl chloride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 213692-95-6 (4S,5R)-4-[3-(4-Methoxy-benzyloxy)-propyl]-2,2-dimethyl-oxazolidine-5-carboxylic acid ethyl ester 
• 213692-98-9 N-[(S)-4-(4-Methoxy-benzyloxy)-1-vinyl-butyl]-acetamide 
• 213692-97-8 (S)-4-(4-Methoxy-benzyloxy)-1-vinyl-butylamine 
• 805247-70-5 (2S,3S)-2-azido-3-hydroxy-6-(4-methoxy-benzyloxy)-hexanoic acid ethyl ester 
• 805247-69-2 (4R,5S)-5-[3-(4-Methoxy-benzyloxy)-propyl]-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 
• 1053253-87-4 Methanesulfonic acid (4S,5S)-4-[3-(4-methoxy-benzyloxy)-propyl]-2-phenyl-[1,3]dioxan-5-yl ester 
• 831228-12-7 (4S,5R)-5-azido-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxane 
• 831228-11-6 (4S,5S)-4-[3-(4-methoxybenzyloxy)propyl]-2-phenyl-1,3-dioxan-5-ol 
• 831228-16-1 tert-Butyl-{(2R,3R)-3-[3-(4-methoxy-benzyloxy)-propyl]-oxiranylmethoxy}-dimethyl-silane 
• 831228-10-5 (2S,3S)-6-(4-methoxybenzyloxy)hexane-1,2,3-triol 
• 1054667-07-0 Methanesulfonic acid 3-((4S,5R)-5-azido-2-phenyl-[1,3]dioxan-4-yl)-propyl ester 
• 1053631-41-6 3-((4S,5R)-5-Azido-2-phenyl-[1,3]dioxan-4-yl)-propan-1-ol 
• 476171-45-6 (2R,3R)-{3-[3-(4-methoxybenzyloxy)propyl]oxiranyl}methanol 
• 208649-02-9 (2S,3S)-3-hydroxypipecolic acid 

Relevant academic research and scientific papers

Sequential one-pot isomerization-Wittig olefination-hydrogenation

Primary allylic alcohols are isomerized to aldehydes in the presence of Pd(OH)2 and homologated to α,β-unsaturated carbonyl derivatives in one-pot by addition of stabilized Wittig ylides in a sequential fashion. When the reaction was prolonged

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.

Total synthesis of microcarpalide

An efficient, convergent approach for the total synthesis of microcarpalide (1) is described. The synthetic strategy features the Sharpless asymmetric dihydroxylation, regioselective epoxide opening with various nucleophiles such as a lithium acetylide and cuprates derived from the vinyl stannane and the vinyl iodide for the construction of a C7-C8 trans-double bond and Yamaguchi macrolactonization as the key steps.

Efficient total synthesis of sapinofuranone B

(Chemical Equation Presented) An efficient enantioselective synthesis of sapinofuranone B (1) using Sharpless asymmetric dihydroxylation, Sonogashira coupling, and Wittig olefination as the key steps is described.

Asymmetric synthesis of both the enantiomers of trans-3-hydroxypipecolic acid

(Chemical Equation Presented). Both the enantiomers of trans-3- hydroxypipecolic acid have been synthesized employing the Sharpless asymmetric dihydroxylation and epoxidation as the key steps starting from a commercially available starting material 1,4-bu

One-pot regio- and stereoselective cyclization of 1,2,n-triols

A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright

An asymmetric dihydroxylation route to (2S,3S)-3-hydroxypipecolic acid

A concise enantioselective synthesis of (2S,3S)-3-hydroxypipecolic acid 1 starting from 1,4-butanediol using Sharpless asymmetric dihydroxylation and the regioselective nucleophilic opening of a cyclic sulfate as the key steps is described. A concise enan

Asymmetric synthesis of anti-convulsive drug (S)-Vigabatrin

An asymmetric synthesis of fully protected (S)-Vigabatrin is described using Sharpless asymmetric aminohydroxylation and reductive elimination of α-oxyβ-amino carbonylhydrazone as key steps.