689277-84-7

Basic information

• Product Name: (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone
• Synonyms: (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone
• CAS NO: 689277-84-7
• Molecular Weight: 602.916
• Mol File: 689277-84-7.mol

Chemical Properties

• CAS DataBase Reference: (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone(689277-84-7)
• EPA Substance Registry System: (7'S,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone(689277-84-7)

Safety Data

• Hazardous Substances Data: 689277-84-7(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 20268-71-7 (7’S,8R,8’R)-4,4’,7’-trihydroxy-3,3’-dimethoxylignano-9,9’-lactone 
• 689277-83-6 (-)-8-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}-8'-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxybenzyl]dihydrofuran-2-one 
• 689277-82-5 (-)-(2S,5S)-thiocarbonic acid O-(2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-enyl) ester O-[4''-(tert-butyldimethylsilanyloxy)-3''-methoxyphenyl] ester 
• 689277-80-3 (-)-(2S,5S)-2-{(tert-butyldimethylsilanyloxy)-[4'-(tert-butyldimethylsilanyloxy)-3'-methoxyphenyl]methyl}but-3-en-1-ol 
• 113931-97-8 4-<(tert-butyldimethylsilyl)oxy>-3-methoxybenzyl bromide 
• 69404-94-0 O-tert-butyldimethylsilylvanillin 
• 877438-38-5 (3R)-3-[(propane-1,3-diyldithio)-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)methyl]butano-4-lactone 
• 877438-36-3 (3R,4R)-3-[(propane-1,3-diyldithio)-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)methyl]-4-[(1R,2S,5R)-2-(1-methylethyl)-5-methyl-1-cyclohexyloxy]butano-4-lactone 
• 877438-30-7 2-(4-tert-butyldimethylsilanyloxy-3-methoxyphenyl)-1,3-dithiane 
• 877438-34-1 (8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-(propane-1,3-diyldithio)lignano-9,9'-lactone 
• 689277-79-0 (+)-4-benzyl-3-(2-{(tert-butyldimethylsilanyloxy)-[4-(tert-butyldimethylsilanyloxy)-3-methoxyphenyl]methyl}but-3-enoyl)oxazolidin-2-one 

Downstream Products

• 689277-86-9 (8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-3,3'-dimethoxy-7'-oxolignano-9,9'-lactone 
• 689277-85-8 (7'R,8R,8'R)-4,4'-bis(tert-butyldimethylsilanyloxy)-7'-hydroxy-3,3'-dimethoxylignano-9,9'-lactone 
• 580-72-3 matairesinol 
• 1052074-60-8 (7'S,8S,8'R)-4,4'-dihydroxy-8'-hydroxymethyl-3,3'-dimethoxylignano-9,7'-lactone 
• 1052074-47-1 (7'S,8S,8'R)-8'-tert-butyldimethylsilyloxymethyl-4,4'-dihydroxy-3,3'-dimethoxylignano-9,7'-lactone 
• 81623-30-5 (-)-(7R,8R,8'R)-4,4',7-trihydroxy-3,3'-dimethoxylidnano-9,9'-lactone 
• 53250-61-6 7-Oxomatairesinol 

Relevant articles and documents

Convenient preparation and spectroscopic characterization of 7r-hydroxymatairesinol

The preparation of 7R-HMR (allo-hydroxymatairesinol) is reported by: (a) NaBH4 kinetic reduction of 7R/7S diastereomeric mixture; and (b) epimerization of the C7 hydroxyl group by Mitsunobu reaction and subsequent ester hydrolysis. The availability of highly pure target compound (7R-HMR) made it possible to confirm the structure of the target compound and to complete the full spectroscopic characterization.

Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones

The asymmetric synthesis of a series of (7′S,8R,8′R)-7′- hydroxylignano-9,9′-lactones is presented, among them the mammalian lignan (7′S)-hydroxyenterolactone and (7′S)-parabenzlactone, allowing the stereochemistry of natural occurring (-)-parabenzlactone

Radical carboxyarylation approach to lignans. Total synthesis of (-)-arctigenin, (-)-matairesinol, and related natural products

Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)α-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.