104307-13-3

Basic information

• Product Name: tribenzyl okadaic acid
• Synonyms: tribenzyl okadaic acid
• CAS NO: 104307-13-3
• Molecular Weight: 1075.39
• Mol File: 104307-13-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tribenzyl okadaic acid(CAS DataBase Reference)
• NIST Chemistry Reference: tribenzyl okadaic acid(104307-13-3)
• EPA Substance Registry System: tribenzyl okadaic acid(104307-13-3)

Safety Data

• Hazardous Substances Data: 104307-13-3(Hazardous Substances Data)

Upstream product

• 102795-14-2 (2S,6R,8S,11R)-2-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-11-benzyloxy-4-methyl-8-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethyl)-1,7-dioxa-spiro[5.5]undec-4-ene 
• 95791-14-3 3-((4aR,6R,7R,8S,8aR)-7-Benzyloxy-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionaldehyde 
• 104307-00-8 C₅₇H₆₄O₈Si 
• 104306-97-0 (R)-1-((4aR,6R,7R,8S,8aR)-7-Benzyloxy-8-methoxymethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-(1-ethoxy-ethoxy)-heptan-3-one 
• 115369-32-9 (R)-1-((2R,3R,4R,5R,6R)-3-Benzyloxy-5-hydroxy-6-hydroxymethyl-4-methoxymethoxy-tetrahydro-pyran-2-yl)-7-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-heptan-3-one 
• 109413-94-7 C₃₈H₅₀O₈Si 
• 104306-99-2 C₃₁H₄₄O₈Si 
• 115352-18-6 C₇₄H₉₈O₁₅S 
• 115352-20-0 C₆₅H₈₈O₁₂ 
• 115352-13-1 C₅₇H₇₄O₁₂SSi 
• 115352-14-2 C₅₆H₈₀O₁₁Si 
• 115352-16-4 C₄₉H₇₂O₁₁Si 
• 115352-17-5 C₅₀H₇₄O₁₀Si 
• 115352-15-3 C₄₉H₇₄O₁₁Si 

Downstream Products

• 78111-17-8 okadaic 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.

SYNTHESIS OF A MARINE POLYETHER TOXIN, OKADAIC ACID (4).TOTAL SYNTHESIS.

Three segments A, B and C for okadaic acid synthesis were coupled with each other in order of A+(B+C), the key steps of the twice couplings being between sulfone carbanions and aldehydes.After the B+C coupling , the asymmetric center C-27 was generated by a hydride reduction of the corresponding ketone 16 under electronic control.The second coupling was followed to form the C-14/15 double bond.Oxidation of the α-oxy aldehyde 36 into the carboxylic acid group was achieved with sodium chlorite without C-1/C-2 bond cleavage.The total synthesis of okadaic acid was accomplished in 106 steps from commercially available D-glucose derivative s and butyne-diol.