289666-94-0

Basic information

• Product Name: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal
• Synonyms: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal
• CAS NO: 289666-94-0
• Molecular Weight: 576.805
• Mol File: 289666-94-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal(289666-94-0)
• EPA Substance Registry System: (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanal(289666-94-0)

Safety Data

• Hazardous Substances Data: 289666-94-0(Hazardous Substances Data)

Upstream product

• 4957-71-5 (+)-(2R,3R)-1,2-O-isopropylidene-4-pentyne-1,2,3-triol 
• 108341-87-3 (2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol 
• 143788-59-4 (2R,3S)-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 
• 143706-60-9 (2R,3R)-3-O-acetyl-1,2-O-isopropylidene-5-(trimethylsilyl)-4-pentyne-1,2,3-triol 
• 289666-92-8 (+)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-4,6-methylenedioxy-3-trimethylsilyloxyheptanoate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 289666-93-9 (-)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate 
• 289667-10-3 (+)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxy-heptanoate 
• 289666-89-3 (-)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-dihydroxypentan-5-yl pivalate 
• 289666-87-1 (+)-(2S,3R,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 
• 289666-88-2 (+)-(2R,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-pentol 
• 289666-86-0 (-)-(2R,3S,4R)-3-benzyloxy-5-tert-butyldiphenylsilyloxy-1,2,4-pentanetriol 
• 289666-90-6 (+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol 
• 289666-91-7 (2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal 

Downstream Products

• 218965-70-9 (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 289667-03-4 (+)-(2R,3R,4R,5S)-1-tert-butyldiphenylsilyloxy-6,6-dimethyl-3-hydroxy-5-methoxy-2,4-methylenedioxyoct-7-en-3-ol 
• 289667-12-5 (1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane 
• 289667-00-1 (+)-(1R,5R,6R,8R,10S)-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 880766-74-5 (1S,5R,6S,8R,10S)-10-methoxy-9,9-dimethyl-5-{[(2R,3R,4RS)-2,3-dimethyl-4-phenylselenylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane 
• 880766-75-6 Benzoic acid (S)-((4S,4aS,6R,8S,8aR)-6-allyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester 
• 289666-99-5 tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane 
• 289666-95-1 (4R,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-5-ol 
• 289667-04-5 (4R,4aR,8S,8aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-8-methoxy-7,7-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-one 
• 289667-11-4 [(4R,5R,6R)-5-Benzyloxy-6-((Z)-(S)-1-methoxy-2,2-dimethyl-pent-3-enyl)-[1,3]dioxan-4-ylmethoxy]-tert-butyl-diphenyl-silane 
• 289667-02-3 (+)-(4S,5R,6R,7R)-6-benzyloxy-8-tert-butyldiphenylsilyloxy-3,3-dimethyl-4-methoxy-5,7-methylenedioxyoctyl-1-ene 

Relevant articles and documents

Convergent total synthesis of (+)-mycalamide A

The details of a convergent total synthesis of (+)-mycalamide A are descri7bed. Yb(OTf)3-TMSCl-catalyzed cross-aldol reaction conditions are used to synthesize the right segment of mycalamide A. In this reaction, an acid-sensitive aldehyde reacts with methyl trimethylsilyl dimethylketene acetal without epimerization to provide the desired aldol adduct. Additionally, a tetrahydropyran ring, which is the left segment of mycalamide A, is prepared using a novel one-pot δ-lactone formation methodology. Both segments are constructed from a common starting material, D-mannitol. These segments are then coupled in the presence of BuLi, and the functional groups are transformed to complete the synthesis of (+)-mycalamide A.

A stereoselective synthesis of the C-10 to C-18 (right-half) fragment of mycalamides employing lewis acid promoted intermolecular aldol reaction.

[reaction: see text] Beginning with D-mannitol, a stereoselective synthesis of the right-half segment of the mycalamides has been accomplished by employing Lewis acid catalyzed intermolecular aldol reaction and oxypalladation as the key steps.