tribenzyl okadaic acid

Base Information

• Chemical Name: tribenzyl okadaic acid
• CAS No.: 104307-13-3
• Molecular Formula: C₆₅H₈₆O₁₃
• Molecular Weight: 1075.39
• Mol file: 104307-13-3.mol

Synonyms:tribenzyl okadaic acid

Chemical Property of tribenzyl okadaic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tribenzyl okadaic acid

There total 66 articles about tribenzyl okadaic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid (194039-27-5) → tribenzyl okadaic acid (104307-13-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1021/ja973286p

Reference yield: 52.0%

C65H86O12 (104307-12-2) → tribenzyl okadaic acid (104307-13-3)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(00)84149-0

Reference yield:

(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 (203926-64-1) → tribenzyl okadaic acid (104307-13-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 20 min, 2.) THF, hexane, -78 deg C, 15 min

2: 1.) NaH

3: n-Bu₃SnH, AIBN / toluene / 2 h / 80 °C

4: 77 percent / aq. Na₂PO₄ buffer, DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.05 h / Irradiation

5: 90 percent / Dess-Marti periodinane, NaHCO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 1.) LiCl, diisopropylethylamine / 1.) CH₃CN, RT, 10 min, 2.) CH₃CN, RT, 20 h

7: (S)-2-methyl-CBS-oxazaborolidine, BF₃*THF / tetrahydrofuran; toluene / 0.08 h / 0 °C

8: p-TsOH*H₂O / benzene / 2 h / Ambient temperature

9: 100 percent / 1M aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature

With lithium hydroxide; boron trifluoride-tetrahydrofuran complex; 2,2'-azobis(isobutyronitrile); Na₂PO₄ buffer; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene;

DOI:10.1021/ja973286p

upstream raw materials:

C₆₅H₈₆O₁₂

1,2-O-(S)-pivalidene-7,24,27-tri-O-benzylokadaic acid

(R)-2-[(R)-2-(4-Methoxy-benzyloxy)-1-methyl-ethyl]-oxirane

(2R,3R)-4-(4-Methoxy-benzyloxy)-3-methyl-butane-1,2-diol

Downstream raw materials:

okadaic acid

Refernces

• 1、 Forsyth,Sabes,Urbanek. "An efficient total synthesis of okadaic acid". . p. 8381 - 8382. Retrieved 2007/10/03.
• 2、 Isobe, Minoru,Ichikawa, Yoshiyasu,Goto, Toshio. "SYNTHETIC STUDIES TOWARD MARINE TOXIC POLYETHERS THE TOTAL SYNTHESIS OF OKADAIC ACID". . p. 963 - 966. Retrieved 2007/10/02.