221696-44-2

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 146916-73-6 (S)-5-((4-methoxybenzyl)oxy)pent-1-en-3-ol 
• 135362-69-5 3-(4-methoxybenzyl)oxypropan-1-ol 
• 1226985-26-7 (+/-)-5-(4-methoxybenzyloxy)pent-1-en-3-ol 
• 1352739-31-1 5-[(4-methoxybenzyl)oxy]pent-1-en-3-one 
• 128461-65-4 3-(p-methoxybenzyloxy)propanal 
• 2746-25-0 p-Methoxybenzyl bromide 
• 119649-27-3 4-((4-methoxybenzyl)oxy)butanal 
• 195257-60-4 (2S)-2-[2-(p-methoxybenzyloxy)ethyl]oxirane 
• 142860-83-1 1-(4-methoxybenzyloxy)-3-butene 
• 824-94-2 p-methoxybenzyl chloride 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 142860-84-2 4-(p-methoxybenzyloxy)-1,2-epoxybutane 
• 193416-58-9 (2S)-4-[(4-methoxybenzyl)oxy]butane-1,2-diol 

Downstream Products

• 1434059-34-3 (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate 
• 1434059-35-4 (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-hydroxypent-4-enoate 

Relevant academic research and scientific papers

Stereocontrolled Total Synthesis of Nonenolide

Nonenolide (1) was first isolated from the entomopathogenic fungus Cordyceps militaries BCC2816 and exhibited good antimalarial activity against Plasmodium falciparum K1. Structurally, it features a decanolide with a trans-double bond attached to two chir

Total synthesis, biological evaluation of dendrodolides A–D and their analogues

A concise total synthesis of dendrodolides A–D (1–4) has been accomplished in 10 steps from commercially available (R)-propylene oxide and 3-buten-1-ol as starting materials. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification and ring-closing metathesis (RCM). In addition, a series of ester derivatives were prepared utilizing Yamaguchi esterification at the C-3 position of the dendrodolide core and screened for their efficacy against cancer cell lines.

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks

An organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.

The first stereoselective synthesis of dendrodolide A

The first stereoselective total synthesis of natural product, dendrodolide A (1) is described from readily available (R)-propylene oxide and 3-buten-1-ol as starting materials. The synthesis was achieved in 10 steps with an overall yield of 19.1%. The key steps involved in the synthesis are Jacobsen hydrolytic kinetic resolution, epoxide ring opening with 2-allyl-1, 3-dithiane, Yamaguchi esterification, and ring-closing metathesis (RCM).

Stereoselective total synthesis of seimatopolide a

Stereoselective total synthesis of the naturally occurring bioactive macrolide, seimatopolide A has been achieved starting from commercially available (+)-diethyl tartrate. Chelation-controlled Grignard reaction, Yamaguchi esterification, ring closing cross metathesis and CBS reduction reactions are involved as key steps.

Total synthesis and revision of the absolute configuration of seimatopolide B

The asymmetric total synthesis of natural seimatopolide B along with its enantiomer is described starting from readily available 5-hexen-1-ol and 3-buten-1-ol. The key steps involved are Jacobson hydrolytic kinetic resolution, proline-catalyzed α-hydroxyl

First asymmetric synthesis of achaetolide

The first asymmetric synthesis of the 10-membered macrolide achaetolide is reported in this article. The main highlight of the synthetic strategy is the ring-closing metathesis (RCM) of intermediate 19, which in turn can be accessed from coupling between alcohol 11 and acid 18. The synthesis of 11 involves enzymatic kinetic resolution (EKR) coupled with a Mitsunobu inversion strategy, while 18 can be prepared by adopting a metal-enzyme combined dynamic kinetic resolution (DKR) reaction followed by functional group manipulation.

Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).

VITAMIN D DERIVATIVES AND PROCESS FOR PRODUCING THE SAME

The object of the present invention is to provide a novel 22-oxavitamin D derivative having a hydroxy group at both 1α- and 3α-positions. According to the present invention, there is provided 22-oxavitamin D derivatives having the following general formul