253663-00-2

Basic information

• Product Name: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal
• Synonyms: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal
• CAS NO: 253663-00-2
• Molecular Weight: 697.384
• Mol File: 253663-00-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal(253663-00-2)
• EPA Substance Registry System: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal(253663-00-2)

Safety Data

• Hazardous Substances Data: 253663-00-2(Hazardous Substances Data)

Upstream product

• 333956-98-2 (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5-(t-butyldimethylsiloxy)-2-chloro-9-hydroxy-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one 
• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 100-39-0 benzyl bromide 
• 60856-63-5 (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 
• 139400-25-2 (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene 
• 163275-31-8 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal 
• 201284-14-2 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol 
• 163275-35-2 Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate 
• 163275-36-3 Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate 
• 599-04-2 (R)-Pantolacton 
• 253662-82-7 (2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-carbaldehyde 
• 253662-80-5 (2R,4S)-2-(4-methoxyphenyl)-5,5-dimethyl-4-vinyl-1,3-dioxane 
• 333956-92-6 (2R,4R)-4-hydroxymethyl-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane 

Downstream Products

• 222726-89-8 (2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 299939-00-7 (2R,3R,5R,6S,7R,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 198711-92-1 (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 253663-02-4 (2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 

Relevant articles and documents

N-tert-Butylbenzenesulfenamide-catalyzed oxidation of alcohols to the corresponding carbonyl compounds with N-chlorosuccinimide

N-tert-Butylbenzenesulfenamide (1)-catalyzed oxidation of various primary and secondary alcohols to the corresponding aldehydes and ketones was efficiently carried out by using N-chlorosuccinimide (NCS) in the coexistence of potassium carbonate and molecular sieves 4? at easy-to-control temperatures ranging from 0°C to room temperature. The present catalytic oxidation was performed without giving any damage to the functional groups in alcohols, and was particularly effective in the oxidation of alcohols that formed labile aldehydes because of its mild reaction conditions. Further, selective oxidation of primary hydroxy groups took place in 1-catalyzed oxidation of several diols. Mechanistic investigation suggested that the chlorination of the sulfenamide 1 by NCS led to the formation of a key species, N-tert-butylbenzenesulfinimidoyl chloride (2), which in turn oxidized alcohols in the presence of potassium carbonate to afford carbonyl products by accompanying regeneration of the catalyst 1.

An effective method for the preparation of optically active polyoxy 8-membered ring enone corresponding to the B ring of taxol

An effective method for the preparation of 8-membered ring enone 1 in sufficient quantities was developed. First, optically active trialkoxyaldehyde 3 was prepared by diastereoselective dihydroxylation of olefin 7 derived from D-pantolactone. Secondly, 8-