163275-41-0

Basic information

• Product Name: (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol
• Synonyms: (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol
• CAS NO: 163275-41-0
• Molecular Weight: 753.18
• Mol File: 163275-41-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol(163275-41-0)
• EPA Substance Registry System: (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol(163275-41-0)

Safety Data

• Hazardous Substances Data: 163275-41-0(Hazardous Substances Data)

Upstream product

• 253662-88-3 (2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-4-[(1S)-1-benzyloxy-2-(t-butyldimethylsiloxy)ethyl]-1,3-dioxane 
• 253662-87-2 (1S)-1-[(2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-yl]ethane-1,2-diol 
• 333956-92-6 (2R,4R)-4-hydroxymethyl-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane 
• 253662-80-5 (2R,4S)-2-(4-methoxyphenyl)-5,5-dimethyl-4-vinyl-1,3-dioxane 
• 253662-82-7 (2R,4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxan-4-carbaldehyde 
• 599-04-2 (R)-Pantolacton 
• 163275-35-2 Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate 
• 201284-14-2 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol 
• 163275-31-8 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal 
• 139400-25-2 (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene 
• 60856-63-5 (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 
• 100-39-0 benzyl bromide 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 31600-43-8 methyl 2-(benzyloxy)acetate 

Downstream Products

• 333956-95-9 (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5,9-bis(t-butyldimethylsiloxy)-2,2-dichloro-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-ol 

Relevant articles and documents

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

An effective method for the preparation of 8-membered ring enone, (4S,5R,7R,8R)-4,8-bis(benzyloxy)-7-(t-butyldimethylsiloxy)-5- (4-methoxybenzyloxy)-2,6,6-trimethylcyclooct-2-enone (1), in sufficient quantities was developed. Optically active trioxy aldehyde, (3R,4S)-4-benzyloxy-5-(t-butyldimethylsiloxy)-3-(4-methoxybenzyloxy)- 2,2-dimethylpentanal (3), was prepared first by diastereoselective dihydroxylation of (2R,4S)-2-(4-methoxyphenyl)-5,5-dimethyl-4-vinyl-1,3-dioxane derived from D-pantolactone. Next, 8-chloro-7-oxoaldehyde, (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(t-butyldimethylsiloxy)-8-chloro-3- (4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal (30), was newly synthesized by the following reactions: i) MgBr2·OEt2-mediated diastereoselective aldol reaction of the aldehyde 3 with (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene and ii) reaction of methyl (2R,3R,5R,6S)-2,6-bis(benzyloxy)-3,7-bis(t-butyldimethylsiloxy)-5- (4-methoxybenzyloxy)-4,4-dimethylheptanoate with 1,1-dichloroethyllithium, followed by successive reductive dehalogenation of thus formed 1,1-dichloroethyl ketone with 1,1-dichloroethyllithium. Then, the chiral 8-chloro-7-oxoaldehyde 30 was converted to the 8-membered ring enone 1 by SmI2-mediated aldol cyclization.

A Novel Approach to the Synthesis of Taxol. A Synthesis of Optically Active 3,7-dibenzyloxy-4,8-di-t-butyl-dimethylsiloxy-5,5-dimethyl-6-p-methoxybenzyloxy-2-octanone by Way of Stereoselective Aldol Reactions

Optically active 3,7-dibenzyloxy-4,8-di-t-butyldimethylsiloxy-5,5-dimethyl-6-p-methoxybenzyloxy-2-octanone (2) has been synthesized by way of diastereoselective aldol reaction between 4-benzyloxy-5-t-butyldimethylsiloxy-2,2-dimethyl-3-p-methoxy-benzyloxypentanal (3) and ketene silyl acetal 4 using MgBr2*OEt2 as a catalyst.The chiral pentanal 3 was synthesized either by asymmetric aldol reaction of both prochiral aldehyde 5 and ketene silyl acetal 4 using a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 6 derived from L-serine andthe lithium enolate derived from methyl isobutyrate.