194039-05-9

Basic information

• Product Name: (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
• Synonyms: (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
• CAS NO: 194039-05-9
• Molecular Weight: 500.632
• Mol File: 194039-05-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(194039-05-9)
• EPA Substance Registry System: (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(194039-05-9)

Safety Data

• Hazardous Substances Data: 194039-05-9(Hazardous Substances Data)

Upstream product

• 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 
• 203926-57-2 ((2S,5R,6R)-5-Benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tert-butyl-diphenyl-silane 
• 203926-59-4 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-6-trimethylsilanyl-hex-5-yn-3-ol 
• 203926-58-3 (R)-2,2-Diethyl-4-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-[1,3]dioxolane 
• 203926-60-7 (2R,3S)-1-(4-Methoxy-benzyloxy)-2-methyl-hex-5-yn-3-ol 
• 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 
• 203926-61-8 (2S,5R,10S,11R)-5-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-12-(4-methoxy-benzyloxy)-11-methyl-10-trimethylsilanyloxy-dodec-7-yn-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 
• 203926-64-1 (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 
• 194038-96-5 (3R,6S)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-one 

Downstream Products

• 194039-24-2 C₇₁H₉₆O₁₄ 
• 78111-17-8 okadaic acid 
• 104307-13-3 tribenzyl okadaic acid 
• 194039-27-5 1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid 

Relevant articles and documents

Efficient synthesis of okadaic acid. 2. Synthesis of the C1-C14 domain and completion of the total synthesis

Described here are the full details of the preparation of a synthetic intermediate representing carbons 1' 14 (C1-C14) of the marine natural product okadaic acid (1), the coupling of this fragment with the previously prepared C15-C38 domain, and the completion of an efficient total synthesis of 1. The C1-C14 intermediate was prepared in 11 steps and ~20% overall yield from a functionalized δ-valerolactone derivative representing C3-C8 of 1. This featured a classic spiroketalization strategy to construct the highly substituted 1,7-dioxaspiro-[5.5]undec-4-ene system, followed by incorporation of the intact C1-C2 α-hydroxyl, α-methyl carboxylate moiety using cis-(S)- lactate pivalidene enolate. The complete C1-C14 intermediate was converted into 1 in five additional steps. Coupling of the C1-C14 fragment with the C15-C38 domain of 1 via C14 aldehyde and C15 β-keto phosphonate moieties provided the complete carbon skeleton of 1 bearing a ketone at C16 and a mixed-methyl acetal at C19. Reduction of the C16 ketone using Corey's (S)- CBS/BH3 system and subsequent acid-triggered spiroketalization formed the Central 1,6-dioxaspiro[4.5]decane ring system. Saponification of the C1-C2 pivalidene group and final reductive cleavage of the three benzyl ethers using lithium di-tert-butylbiphenylide in THF provided 1 in 48% yield from the C1-C14 aldehyde, and in 26 steps and ~2% overall yield in the longest linear sequence from the C22-C27 synthon methyl 3-O-benzyl-α-D- altropyranoside.