96304-95-9

Usage

InChI:InChI=1/C32H55BrO8/c1-20(34)38-28(4,5)23-14-18-30(7,39-23)22(35)13-16-29(6,36)24-10-11-25-31(8,40-24)19-15-26(37-25)32(9)17-12-21(33)27(2,3)41-32/h21-26,35-36H,10-19H2,1-9H3/t21-,22+,23-,24-,25-,26-,29+,30-,31+,32+/m1/s1

Upstream product

• 96304-94-8 thyrsiferyl 18,23-diacetate 
• 306775-68-8 (2S,3S)-1-O-benzyl-2,3-epoxygeraniol 
• 304466-04-4 (R)-1-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-ethane-1,2-diol 
• 240133-55-5 5-bromo-2,6,6-trimethyl-(5R)-tetrahydropyran-2-carbaldehyde 
• 77697-15-5 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 
• 126-90-9 (S)-(+)-linalool 
• 82188-73-6 (2S,3S)-2,3-epoxygeraniol 
• 128243-93-6 Acetic acid 1-((2R,5R)-5-{(1S,4S)-1,4-dihydroxy-4-[(2R,4aR,6R,8aS)-6-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-pentyl}-5-methyl-tetrahydro-furan-2-yl)-1-methyl-ethyl ester 
• 119840-68-5 (2R,4aR,6R,8aS)-Octahydro-3-<(1S,4S)-4-<(2R,5R)-tetrahydro-2-methyl-5-<1-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>ethyl>furan-2-yl>-4-hydroxy-1-(methoxymethoxy)butyl>-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran 
• 119829-49-1 (2R,4aR,6R,8aS)-Octahydro-2-<(1S,4S)-1,4-bis(methoxymethoxy)-4-<(2R,5R)-tetrahydro-2-methyl-5-<1-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>ethyl>furan-2-yl>-1-methylbutyl>-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran 
• 128243-92-5 (2R,4aR,6R,8aS)-2-<(1S,4S)-4-<(2R,5R)-5-(1-Acetoxy-1-methylethyl)tetrahydro-2-methylfuran-2-yl>-1,4-bis(methoxymethoxy)-1-methylbutyl>octahydro-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran 
• 119829-50-4 (2R,4R,6R,8aS)-2-<(1S,4S)-4-<(2R,5R)-Tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methylfuran-2-yl>-1,4-bis(methoxymethoxy)-1-methylbutyl>octahydro-6-<(S)-1-(methoxymethoxy)-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran 
• 304466-03-3 Acetic acid (S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aR,6R,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-butyl ester 
• 304466-01-1 Acetic acid (E)-(S)-1-[(2R,5R)-5-(1-acetoxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4-[(2R,4aR,6R,8aS)-6-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-oxo-but-2-enyl ester 

Downstream Products

• 66873-47-0 Acetic acid (1R,4S)-4-[(4aS,6S,8aR)-6-((2R,5S)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-hydroxy-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentyl ester 
• 66873-39-0 thyrsiferol 

Relevant academic research and scientific papers

Total synthesis of thyrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and an anti-leukemic inducer of apoptosis

A convergent synthetic entry to the squalenoid polyether system has been developed and applied to the biologically active marine natural products thyrsiferyl 23-acetate (1a), thyrsiferol (1b), thyrsiferyl 18-acetate (1c), and thyrsiferyl 18,23-diacetate (

Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol

The first total syntheses of (+)-thyrsiferol (1), (+)-thyrsiferyl 23-acetate (3), and (+)-venustatriol (5) have been accomplished in a stereoselective manner.An effective synthetic scheme to construct the BC ring system, which adopts a chair/twist-boat conformation, was first developed by means of a model study.This method involves stereoselective formation of the strained C ring by intramolecular attack of the C7-hydroxyl group at the C3-postion of the 2,3-epoxy alcohol, employing titanium tetraisopropoxide as an acidic activator.Based on the information accumulated in the model study and retrosynthetic considerations, the total syntheses of 1,3, and 5 were performed in the sequence of (1) construction of the BC ring system equipped with a C1-C6 carbon unit, (2) elongation of the C17-C24 carbon chain, (3) formation of a D ring through the stereoselective epoxidation of the 4-en-1-ol system and successive cyclization, and (4) construction of the A ring by bromonium ion induced cyclization of the 4-en-1-ol system.

EFFECTIVE DEPROTECTION OF 2-(TRIMETHYLSILYLETHOXY)METHYLATED ALCOHOLS (SEM ETHERS). SYNTHESIS OF THYRSIFERYL-23 ACETATE

New conditions for effective cleavage of SEM ethers were developed (TBAF/HMPA in the presence of MS 4A) and usefulness of this reaction was demonstrated by the synthesis of thyrsiferyl-23 acetate.