194038-95-4

Basic information

• Product Name: {(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane
• Synonyms: {(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane
• CAS NO: 194038-95-4
• Molecular Weight: 320.504
• Mol File: 194038-95-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: {(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: {(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane(194038-95-4)
• EPA Substance Registry System: {(S)-1-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-but-3-ynyloxy}-trimethyl-silane(194038-95-4)

Safety Data

• Hazardous Substances Data: 194038-95-4(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 203926-60-7 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-hex-5-yn-3-ol 
• 203926-58-3 (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane 
• 824-94-2 p-methoxybenzyl chloride 
• 135265-40-6 (2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol 
• 135265-42-8 (R)-2-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxirane 
• 247184-60-7 {3-[(4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-prop-1-ynyl}-trimethyl-silane 
• 328535-10-0 (2R,4S,5R)-2-(4-Methoxy-phenyl)-5-methyl-4-prop-2-ynyl-[1,3]dioxane 
• 203926-59-4 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-6-trimethylsilanyl-hex-5-yn-3-ol 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 153185-63-8 (2R,3R)-3,4-diethylmethylenedioxy-2-methyl-butan-1-ol 

Downstream Products

• 194039-01-5 (2S,5R)-5-((S)-{(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 203926-65-2 (2S,5R)-5-({(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 203926-66-3 (2S,5S)-5-({(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-hydroxy-methyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 194039-24-2 C₇₁H₉₆O₁₄ 
• 194039-27-5 1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid 
• 194038-97-6 (2S,5R,10S,11R)-5-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-12-(4-methoxy-benzyloxy)-11-methyl-2,10-bis-trimethylsilanyloxy-dodec-7-yn-6-one 
• 194038-98-7 (Z)-(2S,5R,10S,11R)-5-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-12-(4-methoxy-benzyloxy)-8,11-dimethyl-2,10-bis-trimethylsilanyloxy-dodec-7-en-6-one 
• 194038-99-8 {(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethoxy}-tert-butyl-diphenyl-silane 
• 194039-03-7 (2S,5R)-5-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 203926-68-5 (2S,5R)-5-[(2S,5R,6R,8S)-5-Benzyloxy-8-((R)-2-hydroxy-1-methyl-ethyl)-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl]-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one 
• 194039-05-9 (S)-2-[(2S,6R,8S,11R)-11-Benzyloxy-8-((2S,4R)-2-tert-butyl-4-methyl-5-oxo-[1,3]dioxolan-4-ylmethyl)-4-methyl-1,7-dioxa-spiro[5.5]undec-4-en-2-yl]-propionaldehyde 
• 203926-64-1 (2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-ene-2-carbaldehyde 
• 203926-63-0 {(2S,5R,6S,8S)-5-Benzyloxy-8-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-yl}-methanol 
• 104307-13-3 tribenzyl okadaic acid 

Relevant articles and documents

Expedient access to the okadaic acid architecture: A novel synthesis of the C1-C27 domain

A newly designed synthetic entry to the C1-C27 domain of okadaic acid has been developed. This incorporates substantial improvements in the preparations of the key okadaic acid building blocks representing the C3-C8, C9-C14, and C16-C27 portions. The synthesis of the C3-C8 lactone used (R)-glycidol as the origin of the C4 stereogenic center and featured a late-stage optional incorporation of the C7 hydroxyl group. The complementary C9-C14 fragment was synthesized in a concise route from (R)-3-tert-butyldimethylsilyloxy-2-methylpropanal and propargyl bromide. Assembly of the C3-C14 spiroketal-containing intermediate from the constituent fragments revealed a dramatic effect of C7 functionalization upon spiroketalization efficiency. In contrast, both (9E)- and (9Z)-enones converged readily to the C8 spiroketal upon treatment with acid. Modifications to the central C16-C27 fragment of okadaic acid included the early replacement of benzylic protecting groups by more suitable functionalities to facilitate both the generation of the C15-C27 intermediate and the deprotection of the final products. These modular building blocks were deployed for the synthesis of the C1-C27 scaffold of 7-deoxyokadaic acid. This work demonstrates improvements in the formation of versatile okadaic acid intermediates, as well as a reordering of fragment couplings. This alternative order of coupling was designed to promote the late stage incorporation of nonnatural lipophilic extensions from the C27 terminus.