163275-35-2

Basic information

• Product Name: Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate
• Synonyms: Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate
• CAS NO: 163275-35-2
• Molecular Weight: 666.927
• Mol File: 163275-35-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate(163275-35-2)
• EPA Substance Registry System: Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(tert-butyldimethylsiloxy)-3-hydroxy-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate(163275-35-2)

Safety Data

• Hazardous Substances Data: 163275-35-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 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 
• 201284-14-2 (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol 
• 60856-63-5 (2R)-(-)-3,3-dimethylbutane-1,2,4-triol 
• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 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 
• 178872-58-7 (Z)-2-benzyloxy-1-methoxy-1-(tert-butyldimethylsilyloxy)ethene 

Downstream Products

• 253663-02-4 (2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 163275-36-3 Methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanoate 
• 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 
• 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 
• 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 
• 253662-96-3 (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5,9-bis(t-butyldimethylsiloxy)-2,2-dichloro-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one 
• 253662-98-5 (4R,5R,7R,8S)-4,8-bis(benzyloxy)-5,9-bis(t-butyldimethylsiloxy)-2-chloro-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one 
• 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 
• 253663-00-2 (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal 
• 222726-89-8 (2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 182265-34-5 (2R,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanal 
• 163275-41-0 (2S,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanol 

Relevant articles and documents

Magnesium bromide diethyl etherate mediated highly diastereoselective aldol reaction between an aldehyde and a silyl enol ether

High yield and excellent diastereoselectivity in the formation of methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(t-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybe nzyloxy)-4,4-dimethylheptanoate 3 and methyl (2R,3R,4S)-2,4-dibenzyloxy-3-hydroxypentanoate 7 are achieved by aldol reaction between (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene 1 and chiral alkoxy aldehydes using three equivalents of MgBr2·OEt2. The following mechanism of the above aldol reaction proposes that MgBr2·OEt2 activated both chiral alkoxy aldehydes and silyl enolate, that is, magnesiumu enolate, formed by transmetalation from silyl enolate and MgBr2·OEt2, reacted with MgBr2·OEt2-chelated alkoxy aldehydes via the six-membered cyclic transition state.

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-

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.